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

HRID 2424956Notes

Reaction equation

HRID 2424956 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-3cc99c638c844bbeb2c46cdce5743962
Source dataset
uspto-grants-2011_06
Patent number
US07964622B2

Reaction notes

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