Benzyl 4-Hydroxybenzoate → Benzyl 4-(allyloxy)benzoate

HRID 734412Notes

Reaction equation

HRID 734412 reaction equation
[OH:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])=[CH:4][CH:3]=1.[CH2:18](Br)[CH:19]=[CH2:20].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:20]([O:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])=[CH:4][CH:3]=1)[CH:19]=[CH2:18]

Participants

5

Reactant 3

HCID 7180Benzyl 4-HydroxybenzoateHCID 7841Allyl bromideHCID 11430Potassium Carbonate

Product 1

HCID 22642309Benzyl 4-(allyloxy)benzoateYield 101%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of benzyl 4-hydroxybenzoate (15.00 g, 65.1 mmol) in 130 mL acetone cooled in an ice water bath was added allyl bromide (11.4 mL, 130.1 mmol), followed by portionwise addition of potassium carbonate (45.00 g, 325.3 mmol). The ice bath was removed and the reaction mixture was warmed to rt. The mixture was stirred for 19 h. The precipitates were removed by filtration and the filtrate was concentrated to yield a colorless oil (17.65 g, 100%). LC/MS m/z 269 (M+H)+; 1H NMR (400 MHz, CDCl3) δ 8.00-8.04 (m, 2H), 7.31-7.45 (m, 5H), 6.91-6.94 (m, 2H), 6.00-6.91 (m, 1H), 5.30-5.45 (m, 4H), 4.58-4.61 (m, 2H).

Workup

  1. customThe ice bath was removed
  2. customThe precipitates were removed by filtration
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-5d673c658f74461082bb92da981526ad
Source dataset
uspto-grants-2009_09
Patent number
US07592361B2

Reaction notes

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