Hydrochloric Acid → HCID 69800908, compound

HRID 1268359Notes

Reaction equation

HRID 1268359 reaction equation
[OH:1][CH2:2]/[CH:3]=[CH:4]/[C:5]1[CH:6]=[C:7]([OH:11])[CH:8]=[CH:9][CH:10]=1.Br[CH2:13][C:14]1[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].Cl>CC(C)=O.O>[CH3:21][O:20][C:18](=[O:19])[C:17]1[CH:22]=[CH:23][C:14]([CH2:13][O:11][C:7]2[CH:8]=[CH:9][CH:10]=[C:5](/[CH:4]=[CH:3]/[CH2:2][OH:1])[CH:6]=2)=[CH:15][CH:16]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 256687Methyl 4-(bromomethyl)benzoateHCID 12641156HCID 12641156, compound

Product 1

HCID 69800908HCID 69800908, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A mixture of (E)-3-(3-Hydroxy-propenyl)-phenol (0.5 g, 3.33 mmol), methyl 4-(bromomethyl)benzoate (763 mg, 3.33 mmol) and potassium carbonate (1.8 g, 13.3 mmol) in acetone (40 ml) was stirred at roomtemperature over night. The reaction mixtylre was added water (30 ml) and acidified with 1N HCl and extracted with ethyl acetate (90 ml). The organic phase was washed with water, brine and dried with sodium sulphate and evaporated and dried in vacuo yielding 954 mg (96%) (E)-4-[3-(3-Hydroxy-propenyl)-phenoxymethyl]-benzoic acid methyl ester.

Workup

  1. extractionextracted with ethyl acetate (90 ml)
  2. washThe organic phase was washed with water, brine
  3. dry with materialdried with sodium sulphate
  4. customevaporated
  5. customdried in vacuo

Sources & evidence

ORD record
ord-f0d1259a2b52498793b0987d0107d329
Source dataset
uspto-grants-2003_04
Patent number
US06555577B1

Reaction notes

Loading…