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

HRID 660787Notes

Reaction equation

HRID 660787 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].[CH3:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19]Cl)=[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][CH2:19][C:18]1[CH:21]=[CH:22][C:15]([O:14][CH3:13])=[CH:16][CH:17]=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

Conditions

Temperature
60 °C

Procedure

A mixture of 2-hydroxy-5-methylbenzoic acid methyl ester (4.98 g, 30 mmol), 4-methoxybenzyl chloride (4.69 g, 30 mmol) and K2CO3 (4.55 g, 33 mmol) in DMF (50 mL) is stirred at 60° C. for 48 h. The mixture is diluted with EtOAc and washed with 1N HCl and brine then the organic phase is dried over magnesium sulfate. The solvent is removed under reduced pressure and the residue is purified by column chromatography using a gradient of 0-100% EtOAc/hexane as eluent to give the title compound as a colorless oil.

Workup

  1. washwashed with 1N HCl and brine
  2. dry with materialthe organic phase is dried over magnesium sulfate
  3. customThe solvent is removed under reduced pressure
  4. customthe residue is purified by column chromatography

Sources & evidence

ORD record
ord-df74d21babdf4d7fb4b3e37e2a9c428e
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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