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

HRID 1382526Notes

Reaction equation

HRID 1382526 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 300 ml separable flask 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 140 grams of water. The mixture was reacted at 80° C. for 15 minutes with vigorous stirring. The aqueous alkaline solution of sodium cinnamate thus obtained was poured into a hot funnel which was previously kept at 80° C. The solution was added dropwise with stirring to a beaker having 20 ml of aqueous sulfuric acid solution containing 0.053 mol of sulfuric acid. The resultant suspension was cooled to room temperature and filtered with suction. The crystals were washed with 50 ml of water by stirring in a beaker, filtered and dried under reduced pressure. Cinnamic acid obtained was 14.7 grams (99.9% yield). The purity was above 99.9% according to analysis.

Workup

  1. customThe mixture was reacted at 80° C. for 15 minutes with vigorous stirring

Sources & evidence

ORD record
ord-3a2b9937c4ff432e8e46681ec751544e
Source dataset
uspto-grants-1989_02
Patent number
US04806683

Reaction notes

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