Abigail
September 24th, 2006, 03:25 PM
I`ve converted something from Megas sites, chlorination of the alpha hydrogen in precence of red phosphorus. I would guess it can work with a alkohol instead a carboxylic acid. I belive you can get the upper mentioned compounds by this method.
4-Chloro-1-Butanol:
C4H10O, 108,56 g/mol, bp ~50°C
183 ml 1-butanol is mixed with 10 g red phosphorus in a 500 ml glass flask, connect the flask to a claisen and a reflux
condenser. Connect a thermometer to the adapter and a glass tube to the bottom of the mixture. Put the apparatus to a
sunny place that the flask can receive as much sunlight as possible. After that, a regular current of dryed chlorine is
bubbled through the flask for 12 hours. You can use a chlorine generator and two drying tubes with concentrated H2SO4 to dry the chlorine. To increase the yield the flask is short heated to 45 °C at the end of the reaction. Than the crude 4-chloro-1-butanol is removed from mixture by distillation above 50 °C. The distilate contains somewhat water and remainders of di- and trichloro-1-butanol. Maybe it will work when a few gramm of a anhydrous substance is added to the distilate bevor it purifyed by distillation.
1,4-Dichlorobutane:
C4H8Cl2, 127,01 g/mol, bp: ~155 °C
1,4-dichlorobutane can be prepared exactly as 4-chloro-1-butanol by 209 ml 1-chlorobutane and 10 g red phosphorus.
I don`t know i tinking correct, you can get a alkohol when a solution of potassium or sodium hydroxide
is stirred to the chlorinated substance, the mixture is heated for a while and the crude stuff is than distilled.
1-Butanol:
C4H10O, 74,12 g/mol, bp ~116-117 °C
May be it can prepared from 1-chlorobutane and 1 mol dilute potassium hydroxide solution.
1,4-Butanediol:
C4H10O2, 90,12 g/mol, bp: ~230 °C
1 mol of 4-chloro-1-butanol and 2 mol potassium hydroxide solution.
Does anyone have infos to the conditions to the process ? When this is correct, you can get easy 1,4-Butanediol from 1 mol of dichlorobutane and 2 mol of potassium hydroxide solution.
4-Chloro-1-Butanol:
C4H10O, 108,56 g/mol, bp ~50°C
183 ml 1-butanol is mixed with 10 g red phosphorus in a 500 ml glass flask, connect the flask to a claisen and a reflux
condenser. Connect a thermometer to the adapter and a glass tube to the bottom of the mixture. Put the apparatus to a
sunny place that the flask can receive as much sunlight as possible. After that, a regular current of dryed chlorine is
bubbled through the flask for 12 hours. You can use a chlorine generator and two drying tubes with concentrated H2SO4 to dry the chlorine. To increase the yield the flask is short heated to 45 °C at the end of the reaction. Than the crude 4-chloro-1-butanol is removed from mixture by distillation above 50 °C. The distilate contains somewhat water and remainders of di- and trichloro-1-butanol. Maybe it will work when a few gramm of a anhydrous substance is added to the distilate bevor it purifyed by distillation.
1,4-Dichlorobutane:
C4H8Cl2, 127,01 g/mol, bp: ~155 °C
1,4-dichlorobutane can be prepared exactly as 4-chloro-1-butanol by 209 ml 1-chlorobutane and 10 g red phosphorus.
I don`t know i tinking correct, you can get a alkohol when a solution of potassium or sodium hydroxide
is stirred to the chlorinated substance, the mixture is heated for a while and the crude stuff is than distilled.
1-Butanol:
C4H10O, 74,12 g/mol, bp ~116-117 °C
May be it can prepared from 1-chlorobutane and 1 mol dilute potassium hydroxide solution.
1,4-Butanediol:
C4H10O2, 90,12 g/mol, bp: ~230 °C
1 mol of 4-chloro-1-butanol and 2 mol potassium hydroxide solution.
Does anyone have infos to the conditions to the process ? When this is correct, you can get easy 1,4-Butanediol from 1 mol of dichlorobutane and 2 mol of potassium hydroxide solution.