Trimethyl orthoformate → 4-(2-Carboxyethenyl)benzoic acid

HRID 328920Notes

Reaction equation

HRID 328920 reaction equation
[CH:1]([C:3]1[CH:13]=[CH:12][C:6]([CH:7]=[CH:8][C:9]([OH:11])=[O:10])=[CH:5][CH:4]=1)=[O:2].C(OC)(OC)[O:15]C>CO>[C:1]([C:3]1[CH:13]=[CH:12][C:6]([CH:7]=[CH:8][C:9]([OH:11])=[O:10])=[CH:5][CH:4]=1)([OH:15])=[O:2]

Participants

4

Reactant 2

HCID 9005Trimethyl orthoformateHCID 980772-Propenoic acid, 3-(4-formylphenyl)-

Product 1

HCID 891964-(2-Carboxyethenyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 37.0 g of 4-formylcinnamic acid in 22 ml of trimethyl orthoformate and 600 ml of methanol was heated under reflux for 17 hrs. with stirring. At the end of this time, 100 ml of methanol was added and the reaction mixture was heated under reflux for an additional 5 hrs. and then allowed to cool to room temperature. The precipitate was collected, washed with methanol and dried at 75°-80° overnight to give 7.36 g of 4-carboxycinnamic acid.

Workup

  1. temperatureunder reflux for 17 hrs
  2. temperaturethe reaction mixture was heated
  3. temperatureunder reflux for an additional 5 hrs
  4. customThe precipitate was collected
  5. washwashed with methanol
  6. customdried at 75°-80° overnight

Sources & evidence

ORD record
ord-409c1f137b564fdaa391c6b4c6a40315
Source dataset
uspto-grants-1977_04
Patent number
US04018884

Reaction notes

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