2-Propenoic acid, 3-phenyl-, methyl ester → 2-Propenoic acid, 3-phenyl-

HRID 1382527Notes

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+].C([O-])(=O)C=CC1C=CC=CC=1.[Na+]>S(=O)(=O)(O)O>[C:1]([OH:11])(=[O:10])[CH:2]=[CH:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A 3 l flask equipped with a stirrer was charged with 100.0 grams (0.617 mol) of methyl cinnamate and 1260 grams of aqueous solution containing 25.9 grams (0.647 mol) of sodium hydroxide and vigorously stirred for 15 minutes at 80° C. The obtained aqueous alkaline solution of sodium cinnamate having concentration of 7.7% by weight was added in a lump with 1240 ml of aqueous sulfuric acid solution containing 0.35 ml of sulfuric acid. The resultant slurry having concentration of 3.4% by weight was cooled to room temperature and measured pH to give a value of about 2. The total reaction mixture was discharged and filtered with suction. The separated precipitates were 87.8 grams (96.0% yield) and had purity of above 99.9%. The quantity of cinnamic acid produced per l of water used and per unit volume of the reaction vessel were 36 g/l and 35 g/l respectively.

Workup

customA 3 l flask equipped with a stirrer
temperaturewas cooled to room temperature
customto give a value of about 2
customThe total reaction mixture
filtrationfiltered with suction
customThe separated precipitates

Sources & evidence

ORD record: ord-34666c79aec14f3dbaae44b0dfee8683
Source dataset: uspto-grants-1989_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04806683

Reaction notes

Loading…