Acetone → Dimethyl Ether

HRID 729006Notes

Reaction equation

HRID 729006 reaction equation
[C:1]([C:4]1[CH:31]=[CH:30][C:7]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:26]=[CH:25][C:16]3[CH2:17][CH2:18][CH:19]([C:21]([O:23][CH3:24])=[O:22])[O:20][C:15]=3[C:14]=2[CH2:27][CH2:28][CH3:29])=[C:6]([CH2:32][CH2:33][CH3:34])[C:5]=1[OH:35])(=[O:3])[CH3:2].[CH3:36]C(C)=O.C(=O)([O-])[O-].[K+].[K+].CI>O>[CH3:7][O:8][CH3:9].[C:1]([C:4]1[CH:31]=[CH:30][C:7]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:26]=[CH:25][C:16]3[CH2:17][CH2:18][CH:19]([C:21]([O:23][CH3:24])=[O:22])[O:20][C:15]=3[C:14]=2[CH2:27][CH2:28][CH3:29])=[C:6]([CH2:32][CH2:33][CH3:34])[C:5]=1[O:35][CH3:36])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 180AcetoneHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 13537880HCID 13537880, compound

Product 2

HCID 8254Dimethyl EtherHCID 14475302HCID 14475302, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methyl 7-[3-(4-acetyl-3-hydroxy-2-propyl-phenoxy)propoxy]-3,4-dihydro-8-propyl-2H-1-benzopyran-2-carboxylate (493 mg) was added to 25 ml of acetone containing 276 mg of anhydrous potassium carbonate and 282 mg of methyl iodide. The mixture was refluxed for about 24 hours and water was added and the mixture was then extracted with ethyl acetate. The extract was dried, the solvent removed under vacuum, and the residual oil was chromatographed over silica gel with a 40/60 mixture of ethyl acetate/hexane to provide pure methyl ether, methyl 7-[3-(4-acetyl-3-methoxy-2-propylphenoxy)propoxy]-3,4-dihydro-8-propyl-2H-1-benzopyran-2-carboxylate.

Workup

  1. temperatureThe mixture was refluxed for about 24 hours
  2. extractionthe mixture was then extracted with ethyl acetate
  3. customThe extract was dried
  4. customthe solvent removed under vacuum
  5. customthe residual oil was chromatographed over silica gel with a 40/60 mixture of ethyl acetate/hexane

Sources & evidence

ORD record
ord-2ef1e794446d4388a453458aef925789
Source dataset
uspto-grants-1991_09
Patent number
US05051438

Reaction notes

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