Potassium Carbonate → Methyl 2-(4-methoxybenzyloxy)-5-methylbenzoate

HRID 1642641Notes

Reaction equation

HRID 1642641 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:5]=1[OH:11].Cl[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:5]=1[O:11][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chlorideHCID 89802Methyl 5-methylsalicylate

Product 1

HCID 66756631Methyl 2-(4-methoxybenzyloxy)-5-methylbenzoate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Hydroxy-5-methylbenzoic acid methyl ester (4.98 g, 30 mmol) and 1-chloromethyl-4-methoxybenzene (4.69 g, 30 mmol) and K2CO3 (4.55 g, 33 mmol) in DMF (50 mL) is heated to 60° C. for 72 h. The mixture is then diluted with EtOAc (100 mL), and then washed with 1N HCl solution and brine. It is then dried and concentrated. The residue is purified by flash chromatography to give the title compound as a colorless oil.

Workup

  1. washwashed with 1N HCl solution and brine
  2. customIt is then dried
  3. concentrationconcentrated
  4. customThe residue is purified by flash chromatography

Sources & evidence

ORD record
ord-fd5a46b2cfa84c8f855d228f77ebd2c2
Source dataset
uspto-grants-2012_02
Patent number
US08119666B2

Reaction notes

Loading…