Toluene → HCID 178445659, compound

HRID 528706Notes

Reaction equation

HRID 528706 reaction equation
C[O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([CH2:11][CH:12]([CH3:14])[CH3:13])[CH2:7][CH2:6]1)=[O:4].C1(C)C=CC=CC=1.C[O-].[Na+]>COC(C)(C)C>[CH2:11]([C@H:8]1[CH2:9][CH2:10][C@H:5]([C:3]([OH:4])=[O:2])[CH2:6][CH2:7]1)[CH:12]([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 1140TolueneHCID 10942334Sodium MethoxideHCID 178501084HCID 178501084, compound

Product 1

HCID 178445659HCID 178445659, compound

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

A 2-necked round bottom flask, which had been dried and cooled under argon, was charged with cis/trans-4-isobutyl-cyclohexanecarboxylic acid methyl ester (7:3) (0.5 g, 2.5 mmol), dry toluene (10 ml) and sodium methoxide (0.41 g, 7.6 mmol). The reaction mixture was heated at reflux for 96 h. After cooling to room temperature the mixture was diluted with tert-butyl methyl ether (100 ml) and washed with ice-cold aqueous hydrochloric acid solution (pH 1). The aqueous layer was extracted with one 50-ml portion of tert-butyl methyl ether. The combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo to give the title compound as a (15:85) cis/trans mixture. MS m/e: 183 ([M−H]−)

Workup

  1. customA 2-necked round bottom flask, which had been dried
  2. temperaturecooled under argon
  3. temperatureThe reaction mixture was heated
  4. temperatureat reflux for 96 h
  5. washwashed with ice-cold aqueous hydrochloric acid solution (pH 1)
  6. extractionThe aqueous layer was extracted with one 50-ml portion of tert-butyl methyl ether
  7. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e2519f12e7664a27bdd691bb3df3827f
Source dataset
uspto-grants-2016_05
Patent number
US09346824B2

Reaction notes

Loading…