Carbon Dioxide → Phenylacetic Acid

HRID 2083132Notes

Reaction equation

HRID 2083132 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:8].ClC1C=CC(C)=CC=1.ClCl.[Na].[C:20](=[O:22])=[O:21]>C(Cl)(Cl)(Cl)Cl.O1CCOCC1.C1(C)C=CC=CC=1>[C:3]1([CH2:8][C:20]([OH:22])=[O:21])[CH:4]=[CH:5][CH:6]=[CH:7][CH:2]=1

Participants

9

Reactant 5

HCID 280Carbon DioxideHCID 72382-Chlorotoluene2×HCID 78104-ChlorotolueneHCID 24526ChlorineHCID 5360545Sodium

Product 1

HCID 999Phenylacetic AcidYield 96.3%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 5943Carbon TetrachlorideSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

In accordance with the process of Example 1, 12.7 g of chlorotoluene (a mixture of 67.03% of o-chlorotoluene and 32.97% of p-chlorotoluene) produced by reacting toluene with chlorine in carbon tetrachloride was mixed with 5.4 g of sodium dispersed in 50 ml of 1.4-dioxane. The reaction mixture was heated at 100° C for 3 hours to rearrange the product. The reaction mixture was cooled to 25° C to 28° C and carbon dioxide gas was introduced into the reaction mixture to effect carboxylation with the rearranged product. After the reaction, the post-treatment was carried out in accordance with the process of Example 1 whereby 13.1 g of phenylacetic acid (yield 96.3%) were obtained.

Workup

  1. customproduced
  2. temperatureThe reaction mixture was cooled to 25° C to 28° C
  3. customAfter the reaction

Sources & evidence

ORD record
ord-d5827d1e89d04394bafe22ab646b2b07
Source dataset
uspto-grants-1978_04
Patent number
US04084061

Reaction notes

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