Chloromethyl Methyl Ether → (2-(Methoxymethoxy)phenyl)(phenyl)methanone

HRID 1685332Notes

Reaction equation

HRID 1685332 reaction equation
[OH:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].C([O-])([O-])=O.[K+].[K+].[CH2:22](Cl)[O:23][CH3:24]>CC(C)=O.CCOC(C)=O>[CH3:22][O:23][CH2:24][O:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5]

Participants

6

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 83482'-HydroxybenzophenoneHCID 11430Potassium Carbonate

Product 1

HCID 10444405(2-(Methoxymethoxy)phenyl)(phenyl)methanoneYield 16.5%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
23 °C

Procedure

To a stirring solution of 2-hydroxybenzophenone (3.0 g, 15.1 mmol) and K2CO3 (9.94 g, 71.9 mmol) in acetone (80 mL) under reflux was added MOMCl (2.9 mL, 37.8 mmol) and allowed to stir overnight. The reaction was then cooled to 23° C., diluted with EtOAc, washed with 2N NaOH (3×), the organic phase dried (Na2SO4), filtered and concentrated to provide the product (605 mg) as an oil: 1H NMR (400 MHz, DMSO-d6) δ ppm 7.67-7.72 (2H, m), 7.63 (1H, d, J=7.07 Hz), 7.48-7.54 (3H, m), 7.34 (1H, dd, J=7.33, 1.52 Hz), 7.24 (1H, d, J=8.34 Hz), 7.13 (1H, t, J=7.45 Hz), 5.08 (2H, s), 3.13 (3H, s).

Workup

  1. washwashed with 2N NaOH (3×)
  2. dry with materialthe organic phase dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-84d7fc89dd75416492b408e677a3a89a
Source dataset
uspto-grants-2012_04
Patent number
US08148400B2

Reaction notes

Loading…