Methyl iodide → HCID 21288495, compound

HRID 868426Notes

Reaction equation

HRID 868426 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5](=[O:27])[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][O:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH:20]([OH:26])[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH:15]=2)[CH:7]=1.[CH3:28]I>C(OCC)C>[CH3:3][O:4][C:5](=[O:27])[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][O:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH:20]([O:26][CH3:28])[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH:15]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 21288504HCID 21288504, compound

Product 1

HCID 21288495HCID 21288495, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a suspension of sodium hydride (0.5 g.) in ethyl ether at 0° C. was added methyl-3-[[3-(1-hydroxyhexyl)phenoxy]methyl]benzoate (1.7 g.) in ether. The mixture was allowed to warm to room temperature. Methyl iodide (0.6 ml) was added and the reaction was stirred at room temperature for three days. The reaction was quenched with saturated aqueous ammonium chloride. Th mixture was extracted with ethyl ether. The organic extract was washed with water, dried (MgSO4) and concentrated to an oil. The oil was purified by HPLC on silica gel using a 1:9 ratio of ethyl acetate/hexanes as an eluent.

Workup

  1. customThe reaction was quenched with saturated aqueous ammonium chloride
  2. extractionTh mixture was extracted with ethyl ether
  3. extractionThe organic extract
  4. washwas washed with water
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated to an oil
  7. customThe oil was purified by HPLC on silica gel using a 1:9 ratio of ethyl acetate/hexanes as an eluent

Sources & evidence

ORD record
ord-d1f72e0c40724f4a9c838b6db9ebff06
Source dataset
uspto-grants-1988_10
Patent number
US04778931

Reaction notes

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