M-Cresol → 4-Methoxy-3-(2-m-tolyloxy-acetyl)-benzoic acid methyl ester

HRID 521464Notes

Reaction equation

HRID 521464 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([C:12](=[O:15])[CH2:13]Br)[CH:5]=1.C(=O)([O-])[O-].[K+].[K+].[CH:23]1[C:28]([OH:29])=[CH:27][CH:26]=[CH:25][C:24]=1[CH3:30]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([C:12](=[O:15])[CH2:13][O:29][C:28]2[CH:23]=[C:24]([CH3:30])[CH:25]=[CH:26][CH:27]=2)[CH:5]=1

Participants

5

Reactant 3

HCID 342M-CresolHCID 11430Potassium CarbonateHCID 866547993-(2-Bromo-acetyl)-4-methoxy-benzoic acid methyl ester

Product 1

HCID 670767064-Methoxy-3-(2-m-tolyloxy-acetyl)-benzoic acid methyl esterYield 37.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound of step 1 (1.18 g, 4.12 mmol) and potassium carbonate (1.72 g, 12.4 mmol) were suspended in DMF (10 ml), m-cresol (450 mg, 4.12 mmol) was added, and the mixture was stirred at room temperature for 2 h. The volatiles were evaporated in vacuo, the residue was partitioned between EA and water, and the aqueous phase extracted with EA. The combined organic extracts were washed with a sodium chloride solution, dried over sodium sulfate, filtered and evaporated to dryness. The residue was purified by preparative RP HPLC (water/ACN gradient) to give 0.49 g of the title compound.

Workup

  1. customThe volatiles were evaporated in vacuo
  2. customthe residue was partitioned between EA and water
  3. extractionthe aqueous phase extracted with EA
  4. washThe combined organic extracts were washed with a sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customThe residue was purified by preparative RP HPLC (water/ACN gradient)

Sources & evidence

ORD record
ord-8dc8cba2ab9c44a1baa558c59e743556
Source dataset
uspto-grants-2016_05
Patent number
US09328071B2

Reaction notes

Loading…