Methyl iodide → 1-[2-Methoxy-3-(triphenylmethoxy)propoxy]-4-tetradecylbenzene

HRID 235723Notes

Reaction equation

HRID 235723 reaction equation
[CH2:1]([C:15]1[CH:45]=[CH:44][C:18]([O:19][CH2:20][CH:21]([OH:43])[CH2:22][O:23][C:24]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:17][CH:16]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[H-].[Na+].I[CH3:49]>CN(C)C=O>[CH3:49][O:43][CH:21]([CH2:22][O:23][C:24]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[CH2:20][O:19][C:18]1[CH:17]=[CH:16][C:15]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=[CH:45][CH:44]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 202184241-(4-Tetradecylphenoxy)-3-(triphenylmethoxy)-2-propanol

Product 1

HCID 202185881-[2-Methoxy-3-(triphenylmethoxy)propoxy]-4-tetradecylbenzeneYield 98.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of about 558 mg of 1-(4-tetradecylphenoxy)-3-(triphenylmethoxy)-2-propanol in about 5 ml of dry dimethylformamide was added a prewashed suspension of about 66 mg of sodium hydride in about 2 ml of dimethylformamide followed by about 157 mg of iodomethane. The mixture was stirred under argon for about 2 hours, quenched slowly with water and extracted twice with ether:hexane (about 1:1). The extracts were combined, dried, and the solvents evaporated, giving about 560 mg of the desired title compound.

Workup

  1. customquenched slowly with water
  2. extractionextracted twice with ether
  3. customdried
  4. customthe solvents evaporated

Sources & evidence

ORD record
ord-ef58c5eab1fa4ad5a9e833ba2422906d
Source dataset
uspto-grants-1987_02
Patent number
US04640913

Reaction notes

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