Carbon Dioxide → Phenylacetic Acid

HRID 2083131Notes

Reaction equation

HRID 2083131 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.[Na].[C:10](=[O:12])=[O:11]>C1CCCCC1>[C:5]1([CH2:8][C:10]([OH:12])=[O:11])[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 280Carbon Dioxide2×HCID 78104-ChlorotolueneHCID 5360545Sodium

Product 1

HCID 999Phenylacetic AcidYield 94.1%

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Conditions

Temperature
80 °C

Procedure

In accordance with the process of Example 1, 12.7 g of p-chlorotoluene were contacted and reacted with 5.4 g of sodium dispersed in 50 ml of cyclohexane at 20° C to 30° C and then the reaction mixture was heated to 80° C for 5 hours to rearrange the product. The reaction mixture was cooled to 20° C to 23° C and was gradually poured onto 10 g of solid carbon dioxide with stirring to effect the carbonylation reaction. After the reaction with carbon dioxide, the post-treatment procedure was conducted in accordance with the process of Example 1 to whereby 12.8 g of phenylacetic acid (yield 94.1%) were obtained.

Workup

  1. temperatureThe reaction mixture was cooled to 20° C to 23° C
  2. customthe carbonylation reaction

Sources & evidence

ORD record
ord-dd13c31fe78346f49905649bf3ad16f1
Source dataset
uspto-grants-1978_04
Patent number
US04084061

Reaction notes

Loading…