Methyl iodide → HCID 20131198, compound

HRID 845486Notes

Reaction equation

HRID 845486 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH:11]([CH2:15][OH:16])[C:12]([OH:14])=[O:13])=[CH:5][CH:4]=1.IC.[C:19](=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C>[CH3:19][O:13][C:12](=[O:14])[CH:11]([CH2:15][OH:16])[CH2:10][CH2:9][C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 53987327HCID 53987327, compound

Product 1

HCID 20131198HCID 20131198, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of [4-(4-methoxyphenyl)]-2-hydroxymethyl butanoic acid (6.0 g, 0.027 mol), iodomethane (5.68 g, 0.04 mol) and potassium carbonate (7.45 g, 0.054 mol) in dimethylformamide (40 ml) was heated at 70° C. for 1 h. After cooling to room temperature the reaction mixture was diluted with ethyl acetate (400 ml), washed with water (3×200 ml), sodium hydrogen carbonate solution (2×200 ml) and again with water (2×200 ml). Drying (MgSO4) and removal of solvent at reduced pressure gave the product as a pale yellow oil.

Workup

  1. temperatureAfter cooling to room temperature the reaction mixture
  2. washwashed with water (3×200 ml), sodium hydrogen carbonate solution (2×200 ml) and again with water (2×200 ml)
  3. customDrying
  4. custom(MgSO4) and removal of solvent at reduced pressure

Sources & evidence

ORD record
ord-c88f558f852e46e58f1692dce245eee8
Source dataset
uspto-grants-1988_07
Patent number
US04758573

Reaction notes

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