Benzenebutanol → 4-Phenylbutyric Acid

HRID 1945248Notes

Reaction equation

HRID 1945248 reaction equation
IC1C=CC(C)=CC=1S(O)(=O)=[O:10].OOS([O-])=O.[K+].[C:19]1([CH2:25][CH2:26][CH2:27][CH2:28][OH:29])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>[N+](C)([O-])=O>[C:19]1([CH2:25][CH2:26][CH2:27][C:28]([OH:10])=[O:29])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 76889BenzenebutanolHCID 134448562-Iodo-5-methylbenzene-1-sulfonic acidHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 47754-Phenylbutyric Acid

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Conditions

Temperature
70 °C

Procedure

8.9 mg (0.03 mmol) of 2-iodo-5-methylbenzenesulfonic acid prepared by Preparation Example 2, 2.04 g (3.3 mmol) of powdered Oxone (registered trademark) were added to 3.75 ml of nitromethane, and 450 mg (3 mmol) of 4-phenylbutanol was added dropwise for two hours, and the mixture was heated at 70° C. while being stirred for six hours. The later treatment was carried out in the same way as in Example 1, and then 4-phenylbutanoic acid was obtained. The yield of the obtained 4-phenylbutanoic acid was determined and the result is shown in Table 1.

Workup

  1. additionwas added dropwise for two hours

Sources & evidence

ORD record
ord-a917762cb08e48aa98388375e53bea59
Source dataset
uspto-grants-2013_03
Patent number
US08394995B2

Reaction notes

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