Potassium Hydroxide → 3-(4-Butoxy-3-methoxyphenyl)prop-2-enoic acid

HRID 2308116Notes

Reaction equation

[OH-].[K+].C[O:4][C:5](=[O:21])/[CH:6]=[CH:7]/[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][CH2:17][CH3:18])=[C:10]([O:19][CH3:20])[CH:9]=1>CO.O>[CH2:15]([O:14][C:11]1[CH:12]=[CH:13][C:8](/[CH:7]=[CH:6]/[C:5]([OH:21])=[O:4])=[CH:9][C:10]=1[O:19][CH3:20])[CH2:16][CH2:17][CH3:18]

Participants

Conditions

Temperature: 60 °C

Procedure

10 g (0.15 mmol) potassium hydroxide were dissolved in a mixture of 200 ml methyl alcohol and 5 ml water. 4.85 g (18.35 mmol) (E)-4-butoxy-3-methoxycinnamic acid methyl ester was added. The reaction mixture was subsequently heated to 60° C. After 2.5 h the mixture was concentrated by evaporation. The residue was dissolved in 100 ml cold water and acidified to pH=1 with 13.5 ml hydrochloric acid 37 wt. %. The product was filtered off, washed with water and dried at 50° C. under vacuum to give 4.24 g (92%) (E)-4-butoxy-3-methoxycinnamic acid as white crystals.

Workup

concentrationAfter 2.5 h the mixture was concentrated by evaporation
dissolutionThe residue was dissolved in 100 ml cold water
filtrationThe product was filtered off
washwashed with water
customdried at 50° C. under vacuum

Sources & evidence

ORD record: ord-b522faf5ca3649699744efc2835c2bb8
Source dataset: uspto-grants-2004_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06833421B1

Reaction notes

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