Water → 4-(4-Acetyl-3-hydroxy-2-propylphenoxy)methylcinnamic acid

HRID 615504Notes

Reaction equation

[C:1]([C:4]1[CH:23]=[CH:22][C:7]([O:8][CH2:9][C:10]2[CH:21]=[CH:20][C:13]([CH:14]=[CH:15][C:16]([O:18]C)=[O:17])=[CH:12][CH:11]=2)=[C:6]([CH2:24][CH2:25][CH3:26])[C:5]=1[OH:27])(=[O:3])[CH3:2].O.[OH-].[Li+].C1COCC1.O>CO.Cl>[C:1]([C:4]1[CH:23]=[CH:22][C:7]([O:8][CH2:9][C:10]2[CH:21]=[CH:20][C:13]([CH:14]=[CH:15][C:16]([OH:18])=[O:17])=[CH:12][CH:11]=2)=[C:6]([CH2:24][CH2:25][CH3:26])[C:5]=1[OH:27])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of 1.0 g (2.71 mmol) of methyl 4-(4-acetyl-3-hydroxy-2-propylphenoxy)methylcinnamate and 569 mg (13.57 mmol) of lithium hydroxide, monohydrate, in a mixture of 9 ml of MeOH, 9 ml of THF and 2 ml of water was stirred at 50° C. for 2 hours. The reaction mixture was cooled to room temperature, diluted with 100 ml of 0.5N HCl solution to give a fine white precipitate. The precipitate was isolated by filtration and recrystallized from ethanol to give 750 mg of the title compound as a fine, white cottony solid; mp 203°-204° C.

Workup

temperatureThe reaction mixture was cooled to room temperature
customto give a fine white precipitate
customThe precipitate was isolated by filtration
customrecrystallized from ethanol

Sources & evidence

ORD record: ord-84c749265f3f44018c36f40af242c5b3
Source dataset: uspto-grants-1985_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04499299

Reaction notes

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