Chloromethyl Methyl Ether → HCID 12994199, compound

HRID 2085629Notes

Reaction equation

HRID 2085629 reaction equation
[H-].[Na+].[C:3]([O:8][CH2:9][CH:10]([CH3:12])[CH3:11])(=[O:7])[C@@H:4]([CH3:6])[OH:5].Cl[CH2:14][O:15][CH3:16]>C1(C)C=CC=CC=1>[CH3:14][O:15][CH2:16][O:5][C@H:4]([CH3:6])[C:3]([O:8][CH2:9][CH:10]([CH3:12])[CH3:11])=[O:7]

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 104869892-Methylpropyl-(R)-2-hydroxypropanoate

Product 1

HCID 12994199HCID 12994199, compoundYield 94.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2.0 g of 60% sodium hydride was suspended in 50 ml of toluene. The suspension was cooled on an ice bath. Thereto was dropwise added 7.3 g of isobutyl (R)-(+)-lactate with stirring, followed by stirring for 1 hour. Thereto was dropwise added 5.0 g of chloromethoxymethane, followed by stirring for 3 hours. The reaction mixture was washed with 50 ml of a saturated aqueous sodium hydrogen carbonate solution and 30 ml of water in this order. The washed material was subjected to vacuum distillation to remove the solvent, whereby was obtained 9.0 g (yield: 86.6%) of an oily title compound.

Workup

  1. temperatureThe suspension was cooled on an ice bath
  2. stirringby stirring for 1 hour
  3. stirringby stirring for 3 hours
  4. washThe reaction mixture was washed with 50 ml of a saturated aqueous sodium hydrogen carbonate solution and 30 ml of water in this order
  5. distillationThe washed material was subjected to vacuum distillation
  6. customto remove the solvent

Sources & evidence

ORD record
ord-c6ad584f15d04a208b58726857cd28e4
Source dataset
uspto-grants-2004_04
Patent number
US06720463B1

Reaction notes

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