Dimethylformamide → 1-(Benzyloxy)-2-{[(2,6-dichlorophenyl)methoxy]methyl}butan-2-ol

HRID 1730713Notes

Reaction equation

HRID 1730713 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[C:3]=1[CH2:4][O:5][CH2:6][C:7]([CH3:11])([OH:10])[CH2:8][OH:9].[H-].[Na+].[CH2:19](Cl)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[CH3:27]N(C)C=O>>[Cl:1][C:2]1[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[C:3]=1[CH2:4][O:5][CH2:6][C:7]([CH2:11][CH3:27])([OH:10])[CH2:8][O:9][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 214964103-[(2,6-Dichlorophenyl)methoxy]-2-methylpropane-1,2-diol

Product 1

HCID 214964091-(Benzyloxy)-2-{[(2,6-dichlorophenyl)methoxy]methyl}butan-2-ol

Procedure

1-(2,6-Dichlorobenzyloxymethyl)-1-methylethane-1,2-diol (14g) in dimethyl formamide (80 ml) was treated with sodium hydride (1.3 g) at ambient temperature and stirred for 12 h. Benzyl chloride (8 g) was then added and the reaction mixture stirred for a further 4 h. The solvent was then evaporated and 1-(2,6-dichlorobenzyloxy)-3 -benzyloxy-2-ethylpropan-2-ol isolated as a colourless oil by chromatography on silica gel eluted with 9/1 methylene chloride/ether. The structure was confirmed by n.m.r. techniques.

Workup

  1. stirringthe reaction mixture stirred for a further 4 h
  2. customThe solvent was then evaporated

Sources & evidence

ORD record
ord-85effbd81c1c4bbc952bb3126206249e
Source dataset
uspto-grants-1976_11
Patent number
US03993698

Reaction notes

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