Water → Phenylacetic Acid

HRID 481158Notes

Reaction equation

HRID 481158 reaction equation
[OH2:1].[CH2:2](Cl)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C]=O.CN1CCC[C:14]1=[O:18]>[Pd](Cl)Cl>[C:3]1([CH2:2][C:14]([OH:18])=[O:1])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7503Benzyl ChlorideHCID 13387N-methyl-2-pyrrolidone2×HCID 178418416HCID 178418416, compound2×

Product 1

HCID 999Phenylacetic AcidYield 87%

Reagents, catalysts & solvents 1

HCID 24290Palladium ChlorideCatalyst

Procedure

11.6 g of a solution of 50% by weight of water [321 mmol] in N-methylpyrrolidone are added over a period of 1 hour to a solution of 36.9 g of benzyl chloride [291.5 mmol] and 26 mg of palladium chloride [0.145 mmol] in 76 g of N-methylpyrrolidone at a pressure of 30 bar of carbon monoxide with a temperature of 150° C. in a 300 ml HC4 autoclave. The pressure is kept constant during the addition at 30 bar. After approximately 10 hours of post-stirring, the carbon monoxide uptake is ended. After cooling, a GC yield of 87% phenylacetic acid is obtained. After fractional distillation, 32.1 g of phenylacetic acid [278.7 mmol], equivalent to a practical yield of 81%, are obtained. The melting point is 78° C.

Workup

  1. additionThe pressure is kept constant during the addition at 30 bar
  2. temperatureAfter cooling

Sources & evidence

ORD record
ord-0d1a2fb7e95b4989bd9a4ba9d13505db
Source dataset
uspto-grants-2003_11
Patent number
US06653502B2

Reaction notes

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