Diphenyl Ether → Methyl 2,2-dimethyl-3-(3-allyl-4-hydroxyphenyl)propionate

HRID 581002Notes

Reaction equation

HRID 581002 reaction equation
[CH3:1][C:2]([CH3:18])([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14]CC=C)=[CH:10][CH:9]=1)[C:3]([O:5][CH3:6])=[O:4].[C:19]1(OC2C=CC=CC=2)[CH:24]=CC=C[CH:20]=1>>[CH3:18][C:2]([CH3:1])([CH2:7][C:8]1[CH:9]=[CH:10][C:11]([OH:14])=[C:12]([CH2:24][CH:19]=[CH2:20])[CH:13]=1)[C:3]([O:5][CH3:6])=[O:4]

Participants

3

Reactant 2

HCID 7583Diphenyl EtherHCID 53778250Methyl 2,2-dimethyl-3-(4-allyloxyphenyl)propionate

Product 1

HCID 53903166Methyl 2,2-dimethyl-3-(3-allyl-4-hydroxyphenyl)propionate

Procedure

A solution of methyl 2,2-dimethyl-3-(4-allyloxyphenyl)propionate (1.56 g) in diphenyl ether was heated at reflux for 15 minutes. The reaction mixture was cooled to ambient temperature and the reaction mixture was filtered through a silica gel pad. Elution with a 4:1 (v/v) mixture of hexane and ethyl acetate gave methyl 2,2-dimethyl-3-(3-allyl-4-hydroxyphenyl)propionate (1.53 g) as a yellow oil; microanalysis, found: C, 72.2; H, 7.80%; C15H20O3 requires: C, 72.6; H, 8.12%; NMR(CDCl3): 1.15(6H,s), 2.73(2H,s), 3.35(2H,m), 3.63(3H,s), 4.87(1H,s), 5.10(2H,m), 5.95(1H,m), 6.67(1H,m) and 6.83(2H,m); m/z 249 (M+H).

Workup

  1. temperatureat reflux for 15 minutes
  2. filtrationthe reaction mixture was filtered through a silica gel pad
  3. washElution
  4. additionwith a 4:1 (v/v) mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-a87e2e4067104048a98ad16802ef0d59
Source dataset
uspto-grants-1999_07
Patent number
US05919793

Reaction notes

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