Water → 3-(2-Carboxy-2-phenylvinyl)-benzoic acid ethyl ester

HRID 1680039Notes

Reaction equation

HRID 1680039 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH:11]=O)[CH:6]=1)[CH3:2].[C:14]1([CH2:20][C:21]([OH:23])=[O:22])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(N(CC)CC)C.O>C(OC(=O)C)(=O)C>[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH:11]=[C:20]([C:21]([OH:23])=[O:22])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:6]=1)[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 999Phenylacetic AcidHCID 8471TriethylamineHCID 11084437Ethyl 3-formylbenzoate

Product 1

HCID 536885873-(2-Carboxy-2-phenylvinyl)-benzoic acid ethyl esterYield 438.7%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

17.8 g (0.01 mol) of 3-formyl-benzoic acid ethyl ester, 13.6 g (0.1 mol) of phenylacetic acid and 10 g of triethylamine were dissolved in 30 ml of acetic anhydride and the solution was heated to the reflux for 5 hours. After cooling, 300 ml of water were added to the reaction mixture and the mixture was then heated to the boil for 20 minutes. The solid residue was then decanted off hot, and this was recrystallised from methanol, to which a little water had been added. 13 g (43.9% of theory) of 3-(2-carboxy-2-phenylvinyl)-benzoic acid ethyl ester were obtained as light yellow crystals of melting point 139°-140° C. (isomer mixture with a cis proportion of about 90%). ##STR60##

Workup

  1. temperaturethe solution was heated to the
  2. temperaturereflux for 5 hours
  3. temperatureAfter cooling
  4. temperaturethe mixture was then heated to the boil for 20 minutes
  5. customThe solid residue was then decanted off hot
  6. customthis was recrystallised from methanol, to which a little water
  7. additionhad been added

Sources & evidence

ORD record
ord-0a4c9db4739b4fe1bb31e1163076820c
Source dataset
uspto-grants-1981_06
Patent number
US04271186

Reaction notes

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