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Water → 3(E)-[4-Ethoxy-3-Propoxyphenyl]Acrylic Acid

HRID 987873
Notes
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Reaction equation

HRID 987873 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7](/[CH:10]=[CH:11]/[C:12]([O:14]C)=[O:13])=[CH:6][C:5]=1[O:16][CH2:17][CH2:18][CH3:19])[CH3:2].[OH-].[K+].O>CO>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7](/[CH:10]=[CH:11]/[C:12]([OH:14])=[O:13])=[CH:6][C:5]=1[O:16][CH2:17][CH2:18][CH3:19])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 22987083methyl 3(E)-[4-ethoxy-3-propoxyphenyl]acrylate

Product 1

HCID 177755763(E)-[4-Ethoxy-3-Propoxyphenyl]Acrylic Acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

1.0 g (3.78 mmol) of methyl 3(E)-[4-ethoxy-3-propoxyphenyl]acrylate are suspended in 50 ml of a 10% solution of potassium hydroxide in methanol. 2 ml of water are then added and the mixture is heated to 70° C. for 3 hours and then cooled. Thereafter, the reaction mixture is partitioned between diethyl ether and water, the organic phase is washed several times with saturated sodium chloride solution and the combined aqueous phases are adjusted to pH 4 with a 25% hydrochloric acid solution and extracted several times with methylene chloride. The methylene chloride phases are then combined, dried over magnesium sulfate, filtered and evaporated down. This gives 3(E)-[4-ethoxy-3-propoxyphenyl]acrylic acid.

Workup

  1. temperaturecooled
  2. customThereafter, the reaction mixture is partitioned between diethyl ether and water
  3. washthe organic phase is washed several times with saturated sodium chloride solution
  4. extractionextracted several times with methylene chloride
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated down

Sources & evidence

ORD record
ord-8ca57a9e31f24c40a0e88ed4be42db70
Source dataset
uspto-grants-2003_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06632909B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes