Dichloromethane → Decyl glycidyl ether

HRID 466960Notes

Reaction equation

HRID 466960 reaction equation
[CH2:1]([CH:3]1[O:5][CH2:4]1)Br.ClCCl.[OH-].[Na+].[CH2:11]([OH:21])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH2:11]([O:21][CH2:1][CH:3]1[O:5][CH2:4]1)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 81741-DecanolHCID 14798Sodium HydroxideHCID 18430Epibromohydrin

Product 1

HCID 92960Decyl glycidyl ether

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolvent

Procedure

4.23 ml. (0.05 mole) epibromohydrin in a two-phase mixture of 150 ml. dichloromethane, 150 ml. 50% aqueous sodium hydroxide solution and 3.4 g. tetrabutylammonium hydrogen sulphate are mixed at ambient temperature with 9.52 ml. (0.05 mole) decan-1-ol and stirred overnight. The reaction mixture is then diluted with water and the organic phase is separated off, washed with water and evaporated. The oily residue is purified by column chromatography on silica gel with diethyl ether/isohexane (1:15 v/v). Yield 5.0 g. (47% of theory).

Workup

  1. customthe organic phase is separated off
  2. washwashed with water
  3. customevaporated
  4. customThe oily residue is purified by column chromatography on silica gel with diethyl ether/isohexane (1:15 v/v)

Sources & evidence

ORD record
ord-90844d90a9f24b84b768fbe2afe73230
Source dataset
uspto-grants-1992_10
Patent number
US05158942

Reaction notes

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