P2P via 1-Phenyl-2-propanol?

[Rhodium]

Phenyl-2-propanol is easily made from PhMgBr and propylene oxide. Very cheap, all industrial reagents.

[Moriarty]

Retraction!
Who wants to play cops and dope fiends?

[foxy2]

Synthesis of 4,5-dimethylchrysene.    
Newman, Melvin S.   
J. Am. Chem. Soc.  (1940),  62  2295-300. 
Abstract
Details are given of the prepn. of o-MeC6H4CH2OH in 42% yield from PhCH2Cl and trioxymethylene or in 55% yield from o-MeC6H4MgBr; SOCl2 gives 89% of o-MeC6H4CH2Cl; NaCN in dil. EtOH gives 86% of o-MeC6H4CH2CN (I).  PhMgBr and propylene oxide give 60% of PhCH2CHMeOH which with PBr3 yields 63% of PhCH2CHMeBr (II).

Retentive Friedel-Crafts alkylation of benzene with optically active 2-chloro-1-phenylpropane and 1-chloro-2-phenylpropane.    
Masuda, Shinji; Nakajima, Tadashi; Suga, Sohei.   
Bull. Chem. Soc. Jpn.  (1983),  56(4),  1089-94. (In English)

They prepare 1-phenyl-2-propanol from propylene oxide and benzene.

Process for production of 1-phenyl-2-propanol.    
Mamedov, Markaz K.; Gusejnov, Vidadi M.  (USSR).   
U.S.S.R.  (1992),  SU  1778109   Patent in Russian.
Abstract
PhCH2CHMeOH prodn. by adding C6H6 to propylene oxide (I) in the presence of AlCl3 at 5-6° and passing an inert gas through the reaction mixt. was improved to increase the yield and improved the product quality by carrying out the process with 5-6:3:1 C6H6-I-AlCl3 and by using 2 L/min He as the inert gas.

Patent US5223633

This has some complex method of making 1-phenyl-2-propanol which is probably more applicable to more valuable products.


Grignard reactions of phenyloxirane in the presence of titanium tetraisopropoxide.    
Sosnovskii, G. M.; Astapovich, I. V.  
Zh. Org. Khim.  (1992),  28(7),  1377-9.
Abstract
The title reactions gave PhCHXCH2OH (X = Cl, Br, iodo) and HOCHPhCH2I in £90% combined yield after 20 min, and 65-80% PhCH2CHROH (R = Me, Et, Ph) after 6 h.(They are reacting with grignard reagents)

More to come....
Foxy


Those who give up essential liberties for temporary safety deserve neither liberty nor safety

[foxy2]

This should work, although the yeild doesn't seem to bee stellar.
Foxy

Patent US4396627

5. 1-(4-Acetylphenyl) propan-2-one

Chromic acid solution (11.5 ml, made by adding sulphuric acid [7.3 ml] to sodium dichromate [10.0 g] in water [30 ml]  and making up to 50 ml with water) was added to a vigorously stirred solution of 1-(4-acetylphenyl) propan-2-ol (3.8 g) in ether (50 ml) keeping between 25 DEG-30 DEG. The mixture was stirred at ambient temperature for 2 hours, the organic phase was separated, washed with sodium bicarbonate solution and with saturated sodium chloride solution. The dried (MgSO4) solution was evaporated and distilled (2.5 g). b.p. 122 DEG-128 DEG/0.1 mm.
Those who give up essential liberties for temporary safety deserve neither liberty nor safety

[foxy2]

A one pot synthesis unsymmetric secondary alcohols from two grignard reagents
Daniel L. Comins, and William Dernel
Tetrahedron Letters 22(12) 1981 pgs 1085-1088 

Sunnnary: The sequential addition of two Grignard reagents to 2-(N-methyl-N-formyl)-amino-pyridine(1) in tetrahydrofuran provides a high yield one pot synthesis of unsymmetrical
secondary alcohols.

The reaction is easily carried out by adding the first Grignard reagent (1.0 equiv./THF) to a solution of MFAP (1) in tetrahydrofuran at 0'. After a few minutes the second Grignard reagent (1.3 equiv.) is added and the reaction mixture is heated at reflux for 3 hours and then quenched (aqueous 10% HCl). After isolation and purification, good to high yields of sec-alcohols are obtained as indicated in the table.

First Grignard - PhCH2MgCl
Second Grignard - MeMgCl
Yeild 1-phenyl-2-propanol = 73%
Those who give up essential liberties for temporary safety deserve neither liberty nor safety

[karel]

What a nice work appeared in Tetrahedron Letters!

Catalytic aerobic oxidation of alcohols by Fe(NO3)3–FeBr3

Abstract: Selective aerobic oxidation of secondary and benzylic alcohols was efficiently accomplished by the binary catalyst system Fe(NO3)3–FeBr3 under air at room temperature. The oxidation developed in mild conditions and showed good yields. A secondary alcohol even in the presence of a primary one was selectively oxidized.

General procedure: Oxidation reactions catalyzed by Fe(NO3)3 –FeBr3 . A typical experiment was carried out in an open reaction tube provided with a condenser. To the mixture of Fe(NO3 )3·9H2 O (0.1 mmol) and FeBr3 (0.05 mmol) in 5 mL of CH3CN menthol was added (1 mmol). The reaction mixture was stirred under aerial conditions at room temperature. GC was used to follow the reaction. When the reaction was complete, CH2Cl2 was added and the two phases were separated. The aqueous layer was extracted with CH2Cl2. The combined organic layers were washed with water, dried over MgSO4, and the solvent was removed in vacuo. The residue was chromatographed on a silica gel (70–270 mesh ASTM) column, and eluted with ethyl acetate/hexanes using various ratios. All products identified were found to be identical to authentic samples.

Authors used eight aliphatic secondary alcohols and benzyl alcohol with >75% yield.

TL 2002, 4475-4479