Sulfuric Acid → tert-Butyl 3-oxocyclohexanecarboxylate

HRID 1852426Notes

Reaction equation

HRID 1852426 reaction equation
[O-]S([O-])(=O)=O.[Mg+2].S(=O)(=O)(O)O.[O:12]=[C:13]1[CH2:18][CH2:17][CH2:16][CH:15]([C:19]([OH:21])=[O:20])[CH2:14]1.[CH3:22][C:23](O)([CH3:25])[CH3:24]>C(Cl)Cl>[O:12]=[C:13]1[CH2:18][CH2:17][CH2:16][CH:15]([C:19]([O:21][C:23]([CH3:25])([CH3:24])[CH3:22])=[O:20])[CH2:14]1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 6386tert-ButanolHCID 24083Sulfuric acid magnesium salt (1:1)HCID 27602523-Oxocyclohexane-1-carboxylic acid

Product 1

HCID 66791571tert-Butyl 3-oxocyclohexanecarboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Anhydrous MgSO4 (3.4 g, 28 mmol) was suspended in DCM (28.1 mL) and to this vigorously stirred mixture was added concentrated sulfuric acid (0.7 g, 7 mmol). The resulting mixture was allowed to stir at ambient temperature for 30 minutes. 3-Oxocyclohexanecarboxylic acid (1.0 g, 7.0 mmol) was added followed by t-BuOH (2.6 g, 35 mmol). The resulting mixture was allowed to stir for 24 hours before it was filtered and flushed with DCM. The filtrate was washed with water, and the organic layer was again washed with water, brine, dried over anhydrous MgSO4, filtered, and concentrated in vacuo to afford the title compound. The residue was used without further purification.

Workup

  1. stirringto stir for 24 hours before it
  2. filtrationwas filtered
  3. customflushed with DCM
  4. washThe filtrate was washed with water
  5. washthe organic layer was again washed with water, brine
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2de4582edab34338b7e2701149fe439b
Source dataset
uspto-grants-2015_02
Patent number
US08962608B2

Reaction notes

Loading…