Thionyl Chloride → 2-(Octyloxy)propanoyl chloride
Reaction equation
[CH2:1]([O:9][CH:10]([CH3:14])[C:11](O)=[O:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].S(Cl)([Cl:17])=O>>[CH2:1]([O:9][CH:10]([CH3:14])[C:11]([Cl:17])=[O:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]Participants
3
Procedure
10 ml of thionyl chloride was added to 2.0 g of α-octyloxypropionic acid, and the mixture was refluxed under heat for 2 hours. Then, excess thionyl chloride was distilled off to obtain α-octyloxypropionic acid chloride. 20 ml of dry pyridine was added thereto, and a solution of 5.0 g of p-hydroxybenzoic acid dissolved in 40 ml of dry pyridine was further added. After the addition, the mixture was refluxed for 2 hours, charged into ice water, and extracted with benzene. The extract was purified with a silica gel column chromatography to obtain 4-α-octyloxypropanoyloxybenzoic acid.
Workup
- temperaturethe mixture was refluxed
- temperatureunder heat for 2 hours
- distillationThen, excess thionyl chloride was distilled off
Sources & evidence
- ORD record
- ord-7910db526461444a84a7592174db547e
- Source dataset
- uspto-grants-1988_10
- Patent number
- US04775223
Reaction notes
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