Potassium Hydroxide → 4-(Prop-2-en-1-yloxy)benzoic acid

HRID 436647Notes

Reaction equation

HRID 436647 reaction equation
[CH2:1]([O:4][C:5]1[CH:15]=[CH:14][C:8]([C:9]([O:11]CC)=[O:10])=[CH:7][CH:6]=1)[CH:2]=[CH2:3].[OH-].[K+]>O>[CH2:1]([O:4][C:5]1[CH:15]=[CH:14][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1)[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 227685Ethyl 4-(prop-2-en-1-yloxy)benzoate

Product 1

HCID 4606904-(Prop-2-en-1-yloxy)benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture containing 30 g. of ethyl 4-allyloxybenzoate and 180 ml. of 10% aqueous potassium hydroxide solution was stirred and heated on a steam bath for 21/2 hours. The resulting reaction mixture was diluted with one volume of water and filtered through a sintered glass funnel. The filtrate was stirred and acidified with excess concentrated hydrochloric acid. More water was added in order to facilitate stirring. The copious white solid precipitate was collected and dried in a vacuum oven at 60° C. to produce a quantitative yield of 4-allyloxybenzoic acid, m.p. 163°-164° C.

Workup

  1. additionA mixture containing 30 g
  2. temperatureheated on a steam bath for 21/2 hours
  3. customThe resulting reaction mixture
  4. filtrationfiltered through a sintered glass funnel
  5. additionMore water was added in order
  6. stirringto facilitate stirring
  7. customThe copious white solid precipitate was collected
  8. customdried in a vacuum oven at 60° C.

Sources & evidence

ORD record
ord-f5eb470a79df4620a623bfc8d87f8347
Source dataset
uspto-grants-1977_02
Patent number
US04009208

Reaction notes

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