Carbon Dioxide → Sodium Phenylacetate

HRID 2083130Notes

Reaction equation

HRID 2083130 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:8].[Na].C1(C)C=CC=CC=1[Na:16].C([Na])C1C=CC=CC=1.[C:26](=[O:28])=[O:27].[C]=O>>[C:3]1([CH2:8][C:26]([O-:28])=[O:27])[CH:4]=[CH:5][CH:6]=[CH:7][CH:2]=1.[Na+:16]

Participants

7

Reactant 6

HCID 280Carbon DioxideHCID 72382-ChlorotolueneHCID 5360545SodiumHCID 178418416HCID 178418416, compoundHCID 178424341HCID 178424341, compoundHCID 178507086HCID 178507086, compound

Product 1

HCID 23690424Sodium Phenylacetate

Procedure

In the preferred embodiments of the present invention, chlorotoluene is contacted with sodium which is dispersed in an inert organic solvent at 0° C to 50° C, preferably 10° C to 40° C for 5 minutes to 2 hours preferably about 30 minutes to 1 hour. Thereafter, rearrangement of the tolylsodium to benzylsodium is accomplished by heating the reaction mixture to 40° C to 150° C, preferably 50° C to 120° C for 1 hour to 10 hours preferably 3 hours to 7 hours. After the rearrangement reacting, carbon dioxide gas is introduced into the reaction mixture at room temperature or solid carbon oxide is added to the reaction mixture at room temperature and then the reaction is conducted to produce sodium phenylacetate. Thereafter, a mineral acid is added to the reaction mixture to produce phenylacetic acid; as shown in the first embodiment.

Workup

  1. additionis dispersed in an inert organic solvent at 0° C to 50° C, preferably 10° C to 40° C for 5 minutes to 2 hours preferably about 30 minutes to 1 hour
  2. temperatureby heating the reaction mixture to 40° C to 150° C
  3. waitpreferably 50° C to 120° C for 1 hour to 10 hours preferably 3 hours to 7 hours

Sources & evidence

ORD record
ord-1788e3a0b5c9459995eec9821ed7afa0
Source dataset
uspto-grants-1978_04
Patent number
US04084061

Reaction notes

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