Chloromethyl Methyl Ether → HCID 15034822, compound

HRID 1533845Notes

Reaction equation

HRID 1533845 reaction equation
[C:1]1([CH:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8]([OH:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:17][O:18][CH2:19]Cl.C(N(CC)CC)C>ClCCl>[CH3:17][O:18][CH2:19][O:9][C:8](=[O:10])[CH:7]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 8333Diphenylacetic AcidHCID 8471Triethylamine

Product 1

HCID 15034822HCID 15034822, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-5 °C

Procedure

Diphenylacetic acid methoxymethyl ester was prepared in the following manner: to a mixture of 10.0 g (47.1 mmol) diphenylacetic acid and 4.0 ml (4.16 g, 51.8 mmol) of chloromethyl methyl ether in 50 ml of dichloromethane cooled to -5° C. was added 7.2 ml (5.24 g, 51.8 mmol) of triethylamine in 50 ml dichloromethane. The mixture was allowed to warm to room temperature and stir overnight at which point the reaction mixture was washed with aqueous sodium bicarbonate, dried with MgO-MgSO4, and concentrated in vacuo. The residue was distilled to give 7.25 g (28.3 mmol, 60% yield) of the corresponding methoxymethyl ester, bp 135°-140° C./0.1 mm Hg.

Workup

  1. temperatureto warm to room temperature
  2. washwas washed with aqueous sodium bicarbonate
  3. dry with materialdried with MgO-MgSO4
  4. concentrationconcentrated in vacuo
  5. distillationThe residue was distilled

Sources & evidence

ORD record
ord-63a4f25707a2482cb4bcc01bcbf6806d
Source dataset
uspto-grants-1992_02
Patent number
US05085972

Reaction notes

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