Allyl bromide → HCID 54045189, compound

HRID 580987Notes

Reaction equation

HRID 580987 reaction equation
[CH3:1][O:2][C:3](=[O:16])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]([CH2:13][CH:14]=[CH2:15])[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:23](Br)[CH:24]=[CH2:25]>CC(C)=O>[CH3:1][O:2][C:3](=[O:16])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:25][CH:24]=[CH2:23])=[C:8]([CH2:13][CH:14]=[CH2:15])[CH:7]=1

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 54275119HCID 54275119, compound

Product 1

HCID 54045189HCID 54045189, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of methyl-3(3-allyl-4-hydroxyphenyl)propionate (12.3 g), anhydrous potassium carbonate (13.8 g), and allylbromide (8.64 mls) in acetone (300 ml) was stirred at ambient temperature for two days. The reaction mixture was filtered and the residue washed with acetone. The filtrate and washings were combined and evaporated to give methyl-3-(3-allyl-4-allyloxyphenyl)proprionate as a pale yellow oil (14.0 g); NMR: 2.58(2H,t), 2.75(2H,t), 3.31(2H,d), 3.55(3H,s), 4.52(2H,d), 4.95-5.45(4H,m), 5.85-6.11(2H,m), 6.85(1H,d) and 7.0(2H,m).

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe residue washed with acetone
  3. customevaporated

Sources & evidence

ORD record
ord-a454eb22c2894d89890c13afb8d287f2
Source dataset
uspto-grants-1999_07
Patent number
US05919793

Reaction notes

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