Methylparaben → Methyl 4-but-2-ynyloxybenzoate

HRID 1777270Notes

Reaction equation

HRID 1777270 reaction equation
C(=O)([O-])[O-].[K+].[K+].Br[CH2:8][C:9]#[C:10][CH3:11].[OH:12][C:13]1[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=1>CC(=O)CC>[CH2:8]([O:12][C:13]1[CH:14]=[CH:15][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:21][CH:22]=1)[C:9]#[C:10][CH3:11]

Participants

5

Reactant 3

HCID 7456MethylparabenHCID 11430Potassium CarbonateHCID 27568621-Bromo-2-butyne

Product 1

HCID 59324007Methyl 4-but-2-ynyloxybenzoateYield 100%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

13.6 g (98.5 mmol) of potassium carbonate then 9.6 g (65.7 mmol) of 1-bromobut-2-yne are added to a solution containing 10 g (65.7 mmol) of methyl 4-hydroxybenzoate diluted in 250 ml of 2-butanone. The reaction medium is stirred at reflux for 5 h then at ambient temperature for 18 h. After filtration of the salts, the filtrate is concentrated under vacuum. 13.4 g (100%) of methyl 4-but-2-ynyloxybenzoate are obtained in the form of a light-yellow solid.

Workup

  1. temperatureat reflux for 5 h
  2. filtrationAfter filtration of the salts
  3. concentrationthe filtrate is concentrated under vacuum

Sources & evidence

ORD record
ord-935981f93024428a96655058f5e24ce6
Source dataset
uspto-grants-2016_02
Patent number
US09266848B2

Reaction notes

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