Chloromethyl Methyl Ether → HCID 21055334, compound

HRID 2215273Notes

Reaction equation

HRID 2215273 reaction equation
[CH3:1][C@H:2]([CH2:5][S:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[OH:13])[CH2:3][OH:4].[OH-].[Na+].[CH3:16][O:17][CH2:18]Cl>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].ClCCl>[CH3:1][C@H:2]([CH2:5][S:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][CH2:16][O:17][CH3:18])[CH2:3][OH:4]

Participants

6

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 14798Sodium HydroxideHCID 21055328HCID 21055328, compound

Product 1

HCID 21055334HCID 21055334, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

2.47 g (0.012 mol) of 2-(S)-methyl-3-(2-hydroxyphenylthio)propan-1-ol (XXh), 25 ml of dichloromethane, 12.5 ml (0.024 mol) of an aqueous sodium hydroxide solution (2N), 0.55 ml (0.0012 mol) of Aliquat 336 and 0.9 ml (0.012 mol) of chloromethyl methyl ether are introduced into a 100 ml round-bottomed flask. The mixture is stirred at ambient temperature for 24 hours and then the phases are separated. The organic phase is washed successively with an aqueous hydrochloric acid solution (1N), an aqueous sodium hydroxide solution (1N), water and brine and then dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue is purified by flash chromatography on silica gel (eluent: dichloromethane/acetone=96:4). 1.1 g (0.0045 mol) of the title compound (XXIa) are recovered in the form of a white oil.

Workup

  1. customthe phases are separated
  2. washThe organic phase is washed successively with an aqueous hydrochloric acid solution (1N)
  3. dry with materialan aqueous sodium hydroxide solution (1N), water and brine and then dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by flash chromatography on silica gel (eluent: dichloromethane/acetone=96:4)

Sources & evidence

ORD record
ord-6fc9ecec7fa2469795d31f35c7ab7a28
Source dataset
uspto-grants-2006_09
Patent number
US07109234B2

Reaction notes

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