4-Hydroxybenzoic Acid → 4-(3-Butenyloxy)benzoic acid

HRID 1249959Notes

Reaction equation

HRID 1249959 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[OH-].[K+].Br[CH2:14][CH2:15][CH:16]=[CH2:17]>C(O)C.O>[CH2:17]([O:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1)[CH2:16][CH:15]=[CH2:14]

Participants

6

Reactant 3

HCID 1354-Hydroxybenzoic AcidHCID 14797Potassium HydroxideHCID 21241Homoallyl bromide

Product 1

HCID 5444524-(3-Butenyloxy)benzoic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

69.1 g (0.5 mol) of p-hydroxybenzoic acid were dissolved in 400 ml of ethanol and treated with a solution of 56.1 g (1 mol) of KOH in 250 ml of water. The reaction batch was heated under reflux. While so doing 74.26 g (0.55 mol) of 4-bromo-1-butene were slowly added dropwise. After 5 hours the ethanol was removed on a rotary evaporator. The aqueous phase was brought to a pH value of 10 with NaOH and extracted repeatedly with diethyl ether. The aqueous phase was poured into a mixture of 46 ml of concentrated HCl and 500 ml of ice-water. The separated acid was filtered off, washed with a small amount of water and recrystallized from methanol/water (2:1). After drying at 60° C. in a water-jet vacuum 40 g of 4-(but-3-enyloxy)-benzoic acid remained behind as a white powder; phase succession (° C.): C 120 N 141 I.

Workup

  1. temperatureThe reaction batch was heated
  2. temperatureunder reflux
  3. additionwere slowly added dropwise
  4. customAfter 5 hours the ethanol was removed on a rotary evaporator
  5. extractionextracted repeatedly with diethyl ether
  6. additionThe aqueous phase was poured into a mixture of 46 ml of concentrated HCl and 500 ml of ice-water
  7. filtrationThe separated acid was filtered off
  8. washwashed with a small amount of water
  9. customrecrystallized from methanol/water (2:1)
  10. dry with materialAfter drying at 60° C. in a water-jet vacuum 40 g of 4-(but-3-enyloxy)-benzoic acid

Sources & evidence

ORD record
ord-e01391e70a804871a7ea396c6d1ed86d
Source dataset
uspto-grants-2002_01
Patent number
US06335409B1

Reaction notes

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