Potassium Hydroxide → 2,3-Methylenedioxycinnamic acid

HRID 59609Notes

Reaction equation

HRID 59609 reaction equation
[CH2:1]1[O:16][C:15]2[C:3](=[C:4]([CH:12]=[CH:13][CH:14]=2)[CH:5]=[CH:6][C:7]([O:9]CC)=[O:8])[O:2]1.[OH-].[K+]>CO.O>[CH2:1]1[O:16][C:15]2[C:3](=[C:4]([CH:12]=[CH:13][CH:14]=2)[CH:5]=[CH:6][C:7]([OH:9])=[O:8])[O:2]1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 68513084Ethyl 2,3-methylenedioxycinnamate

Product 1

HCID 44510782,3-Methylenedioxycinnamic acidYield 95%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

A solution of ethyl 2,3-methylenedioxycinnamate (3.40 g) in methanol (25 mL) and water (5 mL) was treated with a solution of potassium hydroxide (4.3 g) in water (25 mL). The mixture was stirred overnight at room temperature before being concentrated in vacuo to half its original volume. The concentrate was then acidified with concentrated HCl to give 2,3-methylenedioxycinnamic acid as a colourless solid (2.81 g, 95%) which was collected by filtration and dried overnight under a vacuum.

Workup

  1. concentrationbefore being concentrated in vacuo to half its original volume

Sources & evidence

ORD record
ord-fc64e81e088448169fea17ac58abe58e
Source dataset
uspto-grants-2016_09
Patent number
US09440926B2

Reaction notes

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