Phenylacetic Acid → HCID 343978, compound

HRID 126967Notes

Reaction equation

HRID 126967 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[C:10]1([CH2:16][C:17]([OH:19])=[O:18])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(OC(=O)C)(=O)C>C(N(CC)CC)C>[C:10]1([C:16](=[CH:6][C:5]2[CH:8]=[CH:9][C:2]([Cl:1])=[CH:3][CH:4]=2)[C:17]([OH:19])=[O:18])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 999Phenylacetic AcidHCID 77264-Chlorobenzaldehyde2×HCID 7918Acetic Anhydride

Product 1

HCID 343978HCID 343978, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A mixture of 56.2 g 4-chlorobenzaldehyde, 54.4 g phenylacetic acid, 80 ml acetic anhydride and 40 ml triethylamine was refluxed for 5 hours. Unreacted 4-chlorobenzaldehyde was removed by steam distillation and the residue dissolved in aqueous alcohol and treated with decolourising carbon. Crystals of α-phenyl-4-chlorocinnamic acid were obtained on acidification of the solution. The product was recrystallised from alcohol and found to have a melting point of 202°-4° C. The chlorosulphonyl derivative was prepared according to the method described in Example 1.

Workup

  1. temperaturewas refluxed for 5 hours
  2. customwas removed by steam distillation
  3. dissolutionthe residue dissolved in aqueous alcohol
  4. additiontreated with decolourising carbon

Sources & evidence

ORD record
ord-3c9d1d525c4241308f4373461fe5957a
Source dataset
uspto-grants-1981_03
Patent number
US04254244

Reaction notes

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