Potassium Hydroxide → Benzeneacetic acid, butyl ester

HRID 2295910Notes

Reaction equation

HRID 2295910 reaction equation
[OH-:1].[K+].Cl[C:4](Cl)(Cl)[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.Cl[C:15]1([O:23]CCCC)C=CC=C[CH:16]1[CH:17]=[CH2:18]>C(O)CCC>[C:6]1([CH2:5][C:4]([O:23][CH2:15][CH2:16][CH2:17][CH3:18])=[O:1])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 561092Benzene, (2,2,2-trichloroethyl)-HCID 20474301HCID 20474301, compound

Product 1

HCID 31210Benzeneacetic acid, butyl ester

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

The process of Example 4 was followed, using 45 ml. of butanol, 12.5 g. of potassium hydroxide, and 4.6 g. of 1,1,1-trichloro-2-phenylethane. The reflux was carried on for 8 hours, at 110°. The product was 3.85 g. of rather impure oil, apparently containing some of the 2-chloro-2-butoxystyrene impurity, which was converted to desired product by adding 8 ml. of butanol and 40 ml. of 1 N hydrochloric acid and stirring the mixture for 20 minutes. The layers were separated, and the aqueous was extracted with two 30 ml. portions of diethyl ether. The organics were combined and washed with saturated sodium chloride solution, dried over sodium sulfate and evaporated under vacuum to obtain 4.2 g. of partially purified product, 77% pure by vapor phase chromatography.

Workup

  1. customwas carried on for 8 hours, at 110°

Sources & evidence

ORD record
ord-c0eecb7eca29434f819b9168aff8b882
Source dataset
uspto-grants-1984_01
Patent number
US04426536

Reaction notes

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