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

HRID 1797343Notes

Reaction equation

HRID 1797343 reaction equation
[OH-].[K+].[CH2:3]([O:7][C:8]1[CH:13]=[CH:12][C:11](/[CH:14]=[CH:15]/[C:16]([O:18]C)=[O:17])=[CH:10][C:9]=1[O:20][CH3:21])[CH2:4][CH2:5][CH3:6]>CO.O>[CH2:3]([O:7][C:8]1[CH:13]=[CH:12][C:11](/[CH:14]=[CH:15]/[C:16]([OH:18])=[O:17])=[CH:10][C:9]=1[O:20][CH3:21])[CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 20744699(E)-4-butoxy-3-methoxycinnamic acid methyl ester

Product 1

HCID 59335643-(4-Butoxy-3-methoxyphenyl)prop-2-enoic acidYield 92.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

10 g (0.15 mol) potassium hydroxide were dissolved in a mixture of 200 ml methyl alcohol and 5 ml water. 4.85 g (18.35 mmol) methyl (2E)-3-(4-butoxy-3-methoxyphenyl)-2-propenoate 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%) (2E)-3-(4-butoxy-3-methoxyphenyl)-2-propenoic acid as white crystals.

Workup

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

Sources & evidence

ORD record
ord-3eb8d2ecb42e4d078d565636b72a5d8a
Source dataset
uspto-grants-2006_04
Patent number
US07034098B2

Reaction notes

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