HCl is cheap.
Neutralize the basic solution until slightly acidic, extract the BzOH with organic solvent(toluene?), then perform the second reaction.
Could toluene --> BzCl possibly be easier?
Also starts with an easily available precursor.
Here is some helpful info
Producing Benzyl chloride
Benzyl chloride.
Niki, Senji. (Japan). Japan. Kokai (1977),
JP 52111520 Patent written in Japanese.
Abstract
Cl (146 kg) was introduced into a mixt. of 330 kg PhMe and 3 kg red P over 9 h at 90-5.5° and the mixt. stirred 1 h to give 172 kg PhCH2Cl (purity 99.5%).
Synthesis of benzyl chloride by solid-liquid phase-transfer catalysis method.
Bui Thi Van Nga; Chu Pham Ngoc Son. Dai Hoc Tong Hop Thanh Pho, Ho Chi Minh, Vietnam.
Tap Chi Hoa Hoc (1985), 23(4), 6-7.
CODEN: TCHHDC ISSN: 0378-2336. Journal written in Vietnamese. CAN 105:193306 AN 1986:593306
Abstract
PhCH2Cl [100-44-7] was prepd. by chlorination of PhMe [108-88-3] with Ca(OCl)2 using tetrabutylammonium hydrogen sulfate [32503-27-8] or tetrabutylammonium bromide [1643-19-2] as phase-transfer catalysts. With suitable ratio of PhMe-catalyst, the yield was high and the reaction was quite selective.
Toluene derivatives chlorinated in the side chain.
Besta, Josef; Soulek, Miroslav. (Czech.). Czech. (1979), 2 pp. CODEN: CZXXA9 CS 179600 19790715 Patent written in Czech.
Abstract
Chlorination of PhMe at 20° in the presence .apprx.0.1% (HOCH2CH2)3N (I) gave a mixt. of PhCH2Cl, PhCHCl2 and PhCCl3. Ring chlorination was also suppressed in the presence of I and Fe3+.
Studies in catalytic reactions of carbons. Part X. Catalytic chlorination of benzene and toluene at ambient temperature in the presence of activated carbons.
Puri, Balwant Rai; Singh, D. D.; Kaura, N. C.; Verma, S. K.
Indian J. Chem., Sect. A (1980), 19A(2), 109-12.
CODEN: IJCADU ISSN: 0376-4710. Journal written in English.
Abstract
Activated C catalyze conversion of C6H6 to PhCl and Cl2C6H4 and that of PhMe to PhCH2Cl on passing Cl through C6H6 or PhMe contg. C in suspension at 25°. The catalytic performance of a C for chlorination of PhMe is enhanced on generation of unsatd. sites on the catalyst either by giving small burn-offs or carrying out surface oxidn. followed by evacuation. The mechanism involves the adsorption of the reactants at unsatd. and other active sites on the surface of C. Chemisorption of Cl during the process leads to deactivation of the C catalysts. The catalytic activity of a C sample is restored on treatment with a H2 current at 500°.
Studies in catalytic reactions of carbons: Part VII. Catalytic chlorination of toluene in presence of active carbons.
Puri, Balwant R.; Singh, D. D.; Verma, S. K.
Indian J. Chem., Sect. A (1978), 16A(12), 1026-9. Journal written in English.
Abstract
The optimum temp. for the title chlorination reaction to give PhCH2Cl is in the 250-400° range. The catalytic performance of a carbon at its optimum temp. varies not so much with surface area as with surface unsatn. Catalytic activity can be enhanced by generation of addnl. unsatd. sites by suitable treatments. The reaction involves dissociative chemisorption of Cl at the unsatd. and other active sites and interaction of toluene vapor with some of the Cl atoms released from the surface under the sweeping action of the gas at elevated temps. As the surface gets increasingly blocked by chemisorbed Cl, the catalytic efficiency falls but can be revived on desorption of Cl by treatment in a current of H2 at 500°.
Benzyl chloride.
Varshaver, E. V.; Kruglova, T. P.; Razumovskii, Yu. V.; Sumin, M. S.; Uskov, V. Ya. (USSR). U.S.S.R. (1979), CODEN: URXXAF SU 644769 19790130 Patent written in Russian.
Abstract
PhCH2Cl was prepd. by chlorination of PhMe at 75-85° in the presence of azobisisobutyronitrile (I) contg. HCONH2 (0.1-0.3 wt.% based on MePH). A 1:2-3 wt. ratio of I-HCONH2 was used to increase the MePh conversion and selectivity to PhCH2Cl.
New catalytic synthesis of benzyl chloride.
Tang, Xun; Shi, Guojun; Liu, Pingmin.
Xiandai Huagong (1997), 17(2), 23-25.
CODEN: HTKUDJ ISSN: 0253-4320. Journal written in Chinese. CAN 127:331230 AN 1997:694942
Abstract
Synthesis of benzyl chloride by catalytic chlorination of toluene with a composite catalyst was reported. The yield of benzyl chloride based on toluene was 92%. The process is superior to thermal-chlorination and photo-chlorination processes.
Highly selective chlorination of toluene to benzyl chloride.
Xu, Zhen. Washington Univ., St. Louis, MO, USA. Avail. UMI, Order No. DA9918677. (1998), 249 pp.
From: Diss. Abstr. Int., B 1999, 60(2), 747. Dissertation written in English. CAN 131:300731 AN 1999:445826
Distillation of benzyl chloride.
Boeckmann, Walter. (Farbenfabriken Bayer A.-G.).
US 3715283 19730206 Patent written in English.
Abstract
Decompn. of PhCH2Cl (I) on distn. of I or mixts. contg. I, esp. in the presence of metal traces, was reduced by addn. of 0.01-1.0% lactams. Thus, on distn. of I from a tech. mixt. of PhMe with aromatic halides with addn. of 0.01-0.05% e-caprolactam, no measurable decompn. of I was obsd.
The decompn. of PhCH2Cl during its distn. or the distn. of its mixts. which is greatly promoted by Fe compds. is strongly inhibited by carrying out the distn. in the presence of a lactam (e.g., 2-pyrrolidone, caprolactam). Thus, 96 wt. % PhCH2Cl is decompd. in 90 min at room temp. when FeCl3 is added to it. With 1.0 wt. % 2-pyrrolidone additive the same decompn. at 95° in 90 min is 13%.
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