Allyl bromide → Ethyl 4-(prop-2-en-1-yloxy)benzoate

HRID 925003Notes

Reaction equation

HRID 925003 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:20][CH:21]=[CH2:22]>CC(C)=O>[CH2:22]([O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:11][CH:12]=1)[CH:21]=[CH2:20]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 8434EthylparabenHCID 11430Potassium Carbonate

Product 1

HCID 227685Ethyl 4-(prop-2-en-1-yloxy)benzoateYield 97%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of ethyl 4-hydroxybenzoate (10.0 g, 60.0 mmol) in acetone (100 mL) was added K2CO3 (33.0 g, 239.1 mmol) at 10° C.; stirred for 0.5 hour. Then 3-bromo-propene (8.0 g, 66.0 mmol) was added dropwise and the reaction mixture was stirred at 10° C. for 5 hours. The resulting mixture was filtered and the filtrate was concentrated under reduced pressure to give product (12.0 g, 96%).

Workup

  1. stirringthe reaction mixture was stirred at 10° C. for 5 hours
  2. filtrationThe resulting mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-95cb13a9e933423e9d4aaa98bdd9e5a1
Source dataset
uspto-grants-2016_03
Patent number
US09283229B2

Reaction notes

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