Hydrochloric Acid → HCID 19744877, compound

HRID 2254224Notes

Reaction equation

HRID 2254224 reaction equation
[OH:1][C:2]1[C:7]([CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11])=[C:6]([O:13][CH3:14])[CH:5]=[CH:4][C:3]=1[C:15](=[O:25])[CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:33][C:34]([O:36][CH3:37])=[O:35].Cl>CC(C)=O>[OH:1][C:2]1[C:7]([CH2:8][CH2:9][CH:10]([CH3:11])[CH3:12])=[C:6]([O:13][CH3:14])[CH:5]=[CH:4][C:3]=1[C:15](=[O:25])[CH2:16][CH2:17][C:18]1[CH:19]=[CH:20][C:21]([O:24][CH2:33][C:34]([O:36][CH3:37])=[O:35])=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 19744890HCID 19744890, compound

Product 1

HCID 19744877HCID 19744877, compoundYield 94.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Then, 32.3 g of 1-(2-hydroxy-4-methoxy-3-isopentylphenyl)-3-(4-hydroxyphenyl)-1-propanone was dissolved in 150 ml of anhydrous acetone, 32.6 g of anhydrous potassium carbonate was added to the solution, and the mixture was stirred for 30 minutes. Then, 17.3 g of methyl α-bromoacetate was added to the reaction mixture, and the mixture was stirred at room temperature for 1 day to effect a reaction. After the reaction, the reaction mixture was neutralized with dilute hydrochloric acid and extracted with ethyl acetate, and the solvent was removed from the extract by distillation to obtain 37.0 g (yield=94.6%) of 1-(2-hydroxy-4-methoxy-3-isopentylphenyl)-3-(4-methoxycarbonylmethoxyphenyl)-1-propanone in the form of a colorless prism.

Workup

  1. stirringthe mixture was stirred at room temperature for 1 day
  2. customa reaction
  3. customAfter the reaction
  4. extractionextracted with ethyl acetate
  5. customthe solvent was removed from the
  6. extractionextract by distillation

Sources & evidence

ORD record
ord-2a510d2e381a41f782f067ae32587fef
Source dataset
uspto-grants-1993_08
Patent number
US05234951

Reaction notes

Loading…