Methyl iodide → 2-Hydroxy-succinic acid 4-(4-allyl-2-methoxy-phenyl)ester 1-methyl ester

HRID 82486Notes

Reaction equation

HRID 82486 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11](=[O:18])[CH2:12][CH:13]([OH:17])[C:14]([OH:16])=[O:15])=[C:6]([O:19][CH3:20])[CH:5]=1)[CH:2]=[CH2:3].[C:21]([O-])([O-])=O.[K+].[K+].CI>CN(C=O)C.C(OCC)(=O)C>[CH3:21][O:15][C:14](=[O:16])[CH:13]([OH:17])[CH2:12][C:11]([O:10][C:7]1[CH:8]=[CH:9][C:4]([CH2:1][CH:2]=[CH2:3])=[CH:5][C:6]=1[O:19][CH3:20])=[O:18]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 673255242-Hydroxy-succinic acid 4-(4-allyl-2-methoxy-phenyl)ester

Product 1

HCID 866749242-Hydroxy-succinic acid 4-(4-allyl-2-methoxy-phenyl)ester 1-methyl esterYield 47%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 2-Hydroxy-succinic acid 4-(4-allyl-2-methoxy-phenyl)ester (0.1 g, 0.35 mmol) in dry DMF (2.0 mL) was added dry K2CO3 followed by methyl iodide (0.024 mL) at 0° C. and the reaction mixture was stirred at room temperature (25° C.) over a period of 60 min. The resulting mixture was diluted with ethyl acetate (50.0 mL) and filtered. The filtrate was washed with water (4×200 mL) and dried over sodium sulphate. The crude product obtained upon evaporation of volatiles was purified by column chromatography to obtain orange colour viscuss liquid (0.05 g, 47%).

Workup

  1. filtrationfiltered
  2. washThe filtrate was washed with water (4×200 mL)
  3. dry with materialdried over sodium sulphate
  4. customThe crude product obtained upon evaporation of volatiles
  5. customwas purified by column chromatography

Sources & evidence

ORD record
ord-0f26233acb6343238e18f505657c36c5
Source dataset
uspto-grants-2014_09
Patent number
US08846721B2

Reaction notes

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