Potassium Hydroxide → 3-[3-(Cyclopentyloxy)-4-methoxyphenyl]acrylic acid

HRID 1073750Notes

Reaction equation

HRID 1073750 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9](/[CH:15]=[CH:16]/[C:17]([O:19]C)=[O:18])[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[K+]>CO.O>[CH:1]1([O:6][C:7]2[CH:8]=[C:9](/[CH:15]=[CH:16]/[C:17]([OH:19])=[O:18])[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 5702848methyl 3-(3-cyclopentoxy-4-methoxyphenyl)-E-propenoate

Product 1

HCID 57121053-[3-(Cyclopentyloxy)-4-methoxyphenyl]acrylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a stirring solution of 0.8 g (2.9 mmol) of methyl 3-(3-cyclopentoxy-4-methoxyphenyl)-E-propenoate in 20 mL of methanol was added dropwise 25 mL of a 1.0 N solution of potassium hydroxide in water over a 5 minute period. The mixture precipitated immediately, but returned to a solution after a 16-hour period at which time the solution was concentrated, diluted with 20 mL of water and neutralized to pH 1.0 with concentrated hydrochloric acid. The analytically pure white solid which formed was collected, washed several times with cold water, and dried in vacuo.

Workup

  1. customThe mixture precipitated immediately
  2. waitreturned to a solution after a 16-hour period at which time
  3. concentrationthe solution was concentrated
  4. additiondiluted with 20 mL of water and neutralized to pH 1.0 with concentrated hydrochloric acid
  5. customThe analytically pure white solid which formed
  6. customwas collected
  7. washwashed several times with cold water
  8. customdried in vacuo

Sources & evidence

ORD record
ord-51e25a6d680d42169ff68d870dc0f7b1
Source dataset
uspto-grants-1990_11
Patent number
US04971959

Reaction notes

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