Potassium Carbonate → Methyl 3-(2-(benzyloxy)ethoxy)-5-methoxybenzoate

HRID 1467040Notes

Reaction equation

HRID 1467040 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([O:12][CH3:13])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].C([O-])([O-])=O.[K+].[K+].Br[CH2:21][CH2:22][O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CN(C=O)C.CCOC(C)=O>[CH2:24]([O:23][CH2:22][CH2:21][O:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([O:12][CH3:13])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 73833Benzene, ((2-bromoethoxy)methyl)-HCID 13941268Methyl 3-hydroxy-5-methoxybenzoate

Product 1

HCID 66746459Methyl 3-(2-(benzyloxy)ethoxy)-5-methoxybenzoateYield 90%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 3-hydroxy-5-methoxybenzoate (Chakraporty, T. K. and Reddy, G. V. J. Org. Chem, 57, 1992, 5462.) (3.3 g, 18.1 mmol) in dry DMF (30 mL) was added K2CO3 (6.3 g, 45.3 mmol) at room temperature. The reaction was stirred at room temperature for 10 minutes then ((2-bromoethoxy)methyl)benzene (3.4 mL, 21.7 mmol) was added and the mixture stirred at 160° C. for 2 hrs. The reaction was cooled down to room temperature and diluted with EtOAc, washed with water and brine, and dried over MgSO4, filtered and concentrated to give the crude product (90%) which was used in the next step without further purification.

Workup

  1. stirringthe mixture stirred at 160° C. for 2 hrs
  2. temperatureThe reaction was cooled down to room temperature
  3. washwashed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9609cf0d800a4fc6bbbfb26a252c6c47
Source dataset
uspto-grants-2015_04
Patent number
US09000054B2

Reaction notes

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