Methanol → HCID 178501084, compound

HRID 528705Notes

Reaction equation

HRID 528705 reaction equation
[CH2:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([C:11]([OH:13])=[O:12])[CH2:7][CH2:6]1)[CH:2]([CH3:4])[CH3:3].[CH3:14]O>S(=O)(=O)(O)O>[CH3:14][O:12][C:11]([C@H:8]1[CH2:9][CH2:10][C@H:5]([CH2:1][CH:2]([CH3:4])[CH3:3])[CH2:6][CH2:7]1)=[O:13]

Participants

4

Reactant 2

HCID 887MethanolHCID 178445659HCID 178445659, compound

Product 1

HCID 178501084HCID 178501084, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

To a solution of cis/trans-4-isobutyl-cyclohexanecarboxylic acid (7:3) (1.0 g, 5.4 mmol) in methanol (54 ml) was added a catalytic amount of sulfuric acid (2 drops). The reaction mixture was heated at reflux for 16 h. The solvent was evaporated. The residue was diluted with tert-butyl methyl ether (100 ml) and washed with aqueous saturated sodium hydrogen carbonate solution (50 ml). The organic layer was dried over anhydrous sodium sulfate and concentrated to dryness to give the title compound ((7:3) cis/trans mixture) as a light yellow oil. MS m/e: 198 (M+)

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 16 h
  3. customThe solvent was evaporated
  4. additionThe residue was diluted with tert-butyl methyl ether (100 ml)
  5. washwashed with aqueous saturated sodium hydrogen carbonate solution (50 ml)
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-0aa9d03c038a4284a1a8f53f1d515a6a
Source dataset
uspto-grants-2016_05
Patent number
US09346824B2

Reaction notes

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