Hydrochloric Acid → Phenylacetic Acid

HRID 1940263Notes

Reaction equation

HRID 1940263 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].CS(OCC([O:13][CH2:14][CH2:15][CH2:16][CH3:17])=O)(=O)=O.Cl.[OH-:19].[Na+]>O.CO.C1C=CC=CC=1>[C:16]1([CH2:15][C:14]([OH:13])=[O:19])[CH:17]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 6451240Aluminum(III) ChlorideHCID 21466675Butyl (methylsulfonyloxy)acetate

Product 1

HCID 999Phenylacetic AcidYield 158.2%

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

19.15 g (0.144 mol) of aluminum chloride are first introduced into 70 ml of benzene at 40°-50° C., and 10 g (0.048 mol) of n-butyl methanesulfonyloxyacetate are then added. The mixture is additionally stirred overnight, hydrolyzed with 10% hydrochloric acid and worked up by the method of Examples 6 to 9. The crude product obtained is refluxed together with 6 g of NaOH in 15 ml of water and 50 ml of methanol for 5 hours. Further workup is carried out as in Examples 6 to 9. 5.17 g (90.3% of theory) of phenylacetic acid are isolated.

Workup

  1. customThe crude product obtained

Sources & evidence

ORD record
ord-625e374c27e349bcaf7a842b14fcb90f
Source dataset
uspto-grants-1997_12
Patent number
US05698735

Reaction notes

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