Potassium Carbonate → HCID 67170342, compound

HRID 1918307Notes

Reaction equation

HRID 1918307 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([OH:12])[CH:5]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:21][C:22]([C:24]1[CH:25]=[C:26]([CH3:30])[CH:27]=[CH:28][CH:29]=1)=[O:23]>CO>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([O:12][CH2:21][C:22](=[O:23])[C:24]2[CH:25]=[C:26]([CH3:30])[CH:27]=[CH:28][CH:29]=2)[CH:5]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 4056967Methyl 3-hydroxy-4-methoxybenzoateHCID 100361292-Bromo-1-(3-methylphenyl)ethan-1-one

Product 1

HCID 67170342HCID 67170342, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-Hydroxy-4-methoxybenzoic acid methyl ester (2.50 g, 13.7 mmol) was dissolved in methanol (20 ml), potassium carbonate (3.72 g, 27.4 mmol) and 2-bromo-1-m-tolyl-ethanone (2.92 g, 13.7 mmol) were added and the mixture was stirred overnight at room temperature. The volatiles were evaporated, the crude material was partitioned between EA and water, the aqueous phase was extracted with EA, the combined organic phases were dried over sodium sulfate and evaporated to dryness. The residue was purified by preparative RP HPLC (water/ACN gradient) to yield the title compound.

Workup

  1. customThe volatiles were evaporated
  2. customthe crude material was partitioned between EA and water
  3. extractionthe aqueous phase was extracted with EA
  4. dry with materialthe combined organic phases were dried over sodium sulfate
  5. customevaporated to dryness
  6. customThe residue was purified by preparative RP HPLC (water/ACN gradient)

Sources & evidence

ORD record
ord-3aa9f4a07a994d55ab9d4c7d11f5810a
Source dataset
uspto-grants-2013_12
Patent number
US08618304B2

Reaction notes

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