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

HRID 742520Notes

Reaction equation

HRID 742520 reaction equation
[CH2:1]([O:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11]C)=[O:10])=[CH:7][CH:6]=1)[CH:2]=[CH2:3].[OH-].[Na+]>C(O)C.O.CO>[CH2:1]([O:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1)[CH:2]=[CH2:3]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 4645407Methyl 4-(allyloxy)benzoate

Product 1

HCID 4606904-(Prop-2-en-1-yloxy)benzoic acidYield 88.1%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

18.0 g (93.6 mmol) of the resulting compound (11) was dissolved in 600 ml of ethanol. The solution was poured into a solution of 12.0 g (300 mmol) of sodium hydroxide dissolved in 80 ml of water and 100 ml of methanol. The whole was refluxed at 80° C. for 2 hours. After removal of the solvent by distillation, the resulting white solid was dissolved in water and the solution was rendered acidic by adding hydrochloric acid, whereby white precipitate formed. The precipitate was extracted with methylene chloride. After removal of the solvent by distillation, the residue was purified by silica gel column chromatography to obtain 4.7 g of p-allyloxybenzoic acid (12) (yield: 88.1%).

Workup

  1. customAfter removal of the solvent
  2. distillationby distillation
  3. dissolutionthe resulting white solid was dissolved in water
  4. additionby adding hydrochloric acid, whereby white precipitate
  5. customformed
  6. extractionThe precipitate was extracted with methylene chloride
  7. customAfter removal of the solvent
  8. distillationby distillation
  9. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-5e0a5666471d4aad90982d053cc08ecb
Source dataset
uspto-grants-1996_09
Patent number
US05554706

Reaction notes

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