Potassium Carbonate → 5-Methoxy-2-(2-methoxy-2-oxoethoxy) benzoic acid, methyl ester

HRID 256338

Reaction equation

HRID 256338 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C(=O)([O-])[O-].[K+].[K+].Br[CH2:21][C:22]([O:24][CH3:25])=[O:23]>CN(C)C=O>[CH3:13][O:12][C:9]1[CH:10]=[CH:11][C:2]([O:1][CH2:21][C:22]([O:24][CH3:25])=[O:23])=[C:3]([CH:8]=1)[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 4072341Methyl 2-hydroxy-5-methoxybenzoate

Product 1

HCID 139617335-Methoxy-2-(2-methoxy-2-oxoethoxy) benzoic acid, methyl esterYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 50.0 g (0.27 mole) of 2-hydroxy-5-methoxybenzoic acid, methyl ester, 88.0 g (0.64 mole) of anhydrous potassium carbonate, and 25.4 ml (46.4 g, 0.30 mole) of methyl bromoacetate in 300 ml of N,N-dimethylformamide is stirred at room temperature for 24 hours. The reaction mixture is added to 1100 g of ice/water, stirred for 1 hour, and the precipitated crude product is filtered and washed with water. Recrystallization from aqueous methanol yields 54.7 g (78% yield) of analytically pure 5-methoxy-2-(2-methoxy-2-oxoethoxy) benzoic acid, methyl ester, mp 82°-85° C.

Workup

  1. stirringstirred for 1 hour
  2. customthe precipitated crude product
  3. filtrationis filtered
  4. washwashed with water
  5. customRecrystallization from aqueous methanol

Sources & evidence

ORD record
ord-ccd8491cf69741ccadee6243ef224d2f
Source dataset
uspto-grants-1987_10
Patent number
US04703053

Linked notes

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