Allyl bromide → Methyl 2,2-dimethyl-3-(4-allyloxyphenyl)propionate

HRID 581001Notes

Reaction equation

HRID 581001 reaction equation
[CH2:1](Br)[CH:2]=[CH2:3].[CH3:5][C:6]([CH3:19])([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1)[C:7]([O:9][CH3:10])=[O:8].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH3:5][C:6]([CH3:19])([CH2:11][C:12]1[CH:13]=[CH:14][C:15]([O:18][CH2:3][CH:2]=[CH2:1])=[CH:16][CH:17]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 53750180HCID 53750180, compound

Product 1

HCID 53778250Methyl 2,2-dimethyl-3-(4-allyloxyphenyl)propionate

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

Allyl bromide (0.66 ml) was added to a stirred suspension of methyl 2,2-dimethyl-3-(4-hydroxyphenyl)propionate (1.41 g) and potassium carbonate (1.08 g) in butan-2-one (12 ml). The reaction mixture was heated at reflux for 19 hours, cooled, and filtered. The filtrate was evaporated to give methyl 2,2-dimethyl-3-(4-allyloxyphenyl)propionate (1.59 g) as an oil; NMR(CDCl3): 1.17(6H,s), 2.78(2H,s), 3.65(3H,s), 4.50(2H,m), 5.33(2H,m), 6.02(1H,m), 6.70(2H,m) and 7.00(2H,m); m/z 248(M+).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 19 hours
  3. temperaturecooled
  4. filtrationfiltered
  5. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-412a153bc7524bd798bfbe56e5430534
Source dataset
uspto-grants-1999_07
Patent number
US05919793

Reaction notes

Loading…