Acetone → 4-Benzyloxy-3-(1-phenyl-vinyl)-benzoic acid-methylester

HRID 394001Notes

Reaction equation

HRID 394001 reaction equation
[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH2:12])[CH:5]=1.[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.CC(C)=O>>[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:6]([C:11]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[CH2:12])[CH:5]=1

Participants

4

Reactant 3

HCID 180AcetoneHCID 7498Benzyl BromideHCID 226484304-Hydroxy-3-(1-phenyl-vinyl)-benzoic acid methylester

Product 1

HCID 226484274-Benzyloxy-3-(1-phenyl-vinyl)-benzoic acid-methylesterYield 80%

Procedure

To a solution of 1.50 g (5.9 mmole) 4-hydroxy-3-(1-phenyl-vinyl)-benzoic acid methylester and 1.04 g (6.1 mmole) benzyl bromide in 10 ml abs. acetone 1.24 g (8.9 mmole) potassium carbonate are added. The reaction mixture is then heated for 4 hours with recycling. Following cooling of the suspension, it is filtered and the residue is washed with 50 ml diethtylether. The solvent is removed and the raw product obtained is cleaned by column chromatography (silica gel, petroleum ether/MTBE=5/1 (v/v)). 1.62 g (4.7 mmole, 80%) 4-benzyloxy-3-(1-phenyl-vinyl)-benzoic acid-methylester are obtained.

Workup

  1. temperatureThe reaction mixture is then heated for 4 hours
  2. temperatureFollowing cooling of the suspension, it
  3. filtrationis filtered
  4. washthe residue is washed with 50 ml diethtylether
  5. customThe solvent is removed
  6. customthe raw product obtained

Sources & evidence

ORD record
ord-d132a7886a8f429ab52896267f2b39ff
Source dataset
uspto-grants-2004_10
Patent number
US06809225B2

Reaction notes

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