Eugenol → HCID 85970746, compound

HRID 82483

Reaction equation

HRID 82483 reaction equation
[C:1]1([O:11][CH3:12])[C:2](=[CH:4][CH:5]=[C:6]([CH:10]=1)[CH2:7][CH:8]=[CH2:9])[OH:3].C([O-])([O-])=O.[K+].[K+].[Br:19][CH2:20][C:21](Br)=[O:22]>ClCCl.C(OCC)(=O)C>[CH2:7]([C:6]1[CH:5]=[CH:4][C:2]([O:3][C:21](=[O:22])[CH2:20][Br:19])=[C:1]([O:11][CH3:12])[CH:10]=1)[CH:8]=[CH2:9]

Participants

6

Reactant 3

HCID 3314EugenolHCID 11430Potassium CarbonateHCID 61147Bromoacetyl bromide

Product 1

HCID 85970746HCID 85970746, compoundYield 63.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of eugenol (500 mg, 3.03 mmol) in dichloromethane (5 mL) were added K2CO3 (1.0 g, 7.57 mmol) followed by bromo acetyl bromide (931 mg, 4.54 mmol) at 0° C. The mixture was allowed to stir at room temperature (25° C.) over a period of 1 hr. The resulting mixture was diluted with ethyl acetate (200 mL), washed with water (2×200 mL) and dried over sodium sulphate. The crude product obtained up on evaporation of the solvent was further purified by silica gel column chromatography to obtain bromo-acetic acid 4-allyl-2-methoxy-phenylester as viscous oil (550 mg, 63%).

Workup

  1. washwashed with water (2×200 mL)
  2. dry with materialdried over sodium sulphate
  3. customThe crude product obtained up on evaporation of the solvent
  4. customwas further purified by silica gel column chromatography

Sources & evidence

ORD record
ord-8f66dd82a7eb4d3ca06188c41d201982
Source dataset
uspto-grants-2014_09
Patent number
US08846721B2

Linked notes

Loading…