2-Propenoic acid, 3-phenyl-, methyl ester → Sodium;3-phenylprop-2-enoate

HRID 1382525Notes

Reaction equation

HRID 1382525 reaction equation
[C:1]([O:11]C)(=[O:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[OH-].[Na+:14]>O>[C:1]([O-:11])(=[O:10])[CH:2]=[CH:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1.[Na+:14]

Participants

4

Reactant 2

HCID 76442-Propenoic acid, 3-phenyl-, methyl esterHCID 14798Sodium Hydroxide

Product 1

HCID 517350Sodium;3-phenylprop-2-enoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A separable flask equipped with a stirrer was charged with 16.2 grams (0.10 mol) of methyl cinnamate, and a solution of 4.3 grams of 97 wt. % sodium hydroxide in 200 grams of water, and the mixture was reacted at 80° C. for 15 minutes with vigorous stirring. The aqueous alkaline solution of sodium cinnamate thus obtained was added slowly under stirring with 200 ml of aqueous sulfuric acid solution containing 0.056 mol of sulfuric acid. The formed suspension had pH of approximately 1.5 after cooling to room temperature. The precipitates were filtered with suction, washed with 50 ml of water by stirring in a beaker, filtered again and dried under reduced pressure. Cinnamic acid thus obtained was 14.6 grams (98.5% yield) and had purity of more than 99.9% according to analysis.

Workup

  1. customA separable flask equipped with a stirrer

Sources & evidence

ORD record
ord-dbc658732be147a2a19755eb1039e5f0
Source dataset
uspto-grants-1989_02
Patent number
US04806683

Reaction notes

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