Acetone → (+/-)-3-[2,4-Bis(methoxymethoxy)phenyl]cyclohexanecarboxylic Acid
Reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[C:9]([O:11][CH2:12][O:13][CH3:14])[CH:8]=[CH:7][C:6]=1[CH:15]1[CH2:20][CH2:19][CH2:18][CH:17]([CH2:21][OH:22])[CH2:16]1.CC(C)=[O:25]>S(=O)(=O)(O)O.[O-2].[Cr+6].[O-2].[O-2]>[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[C:9]([O:11][CH2:12][O:13][CH3:14])[CH:8]=[CH:7][C:6]=1[CH:15]1[CH2:20][CH2:19][CH2:18][CH:17]([C:21]([OH:25])=[O:22])[CH2:16]1Participants
Procedure
A solution of (±)-{3-[2,4-bis(methoxymethoxy)phenyl]cyclohexyl}methanol (50 mg) in acetone (1 ml) was added to a stirred solution of chromium (VI) oxide (64 mg) in 2M sulfuric acid (0.64 ml) at 0° C. over 3 hr. After 3 hr at 0° C. and then 16 hr at room temperature, the reaction mixture was partitioned between water (10 ml) and ethyl acetate (20 ml). The layers were separated and the aqueous layer was extracted with ethyl acetate (2×20 ml). The combined organic extracts were washed with water (20 ml), dried over magnesium sulfate and evaporated in vacuo. The residue was purified by flash column chromatography (SiO2, ethyl acetate/petrol, 4:1 v/v) to give the title compound as a colourless oil (15 mg, 29%). Rf (ethyl acetate/petrol, 4:1 v/v) 0.5.
Workup
- custom16 hr at room temperature, the reaction mixture was partitioned between water (10 ml) and ethyl acetate (20 ml)
- customThe layers were separated
- extractionthe aqueous layer was extracted with ethyl acetate (2×20 ml)
- washThe combined organic extracts were washed with water (20 ml)
- dry with materialdried over magnesium sulfate
- customevaporated in vacuo
- customThe residue was purified by flash column chromatography (SiO2, ethyl acetate/petrol, 4:1 v/v)
Sources & evidence
- ORD record
- ord-754d6dbb2b794bdb9ace01b7d89f66c0
- Source dataset
- uspto-grants-2005_08
- Patent number
- US06933319B2
Reaction notes
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