Sulfuric Acid → 4-Oxocyclohexanecarboxylic acid

HRID 1108667Notes

Reaction equation

HRID 1108667 reaction equation
OS(O)(=O)=O.[O:6]=[C:7]1[CH2:12][CH2:11][CH:10]([C:13]([O:15]CC)=[O:14])[CH2:9][CH2:8]1>>[O:6]=[C:7]1[CH2:12][CH2:11][CH:10]([C:13]([OH:15])=[O:14])[CH2:9][CH2:8]1

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 317638Ethyl 4-oxocyclohexanecarboxylate

Product 1

HCID 1927304-Oxocyclohexanecarboxylic acid

Procedure

A mixture of 2% H2SO4 and ethyl 4-oxo-cyclohexanoate 46 (10.0 g., 58.7 mmole) was stirred vigorously at 80° for 2 hours. The solution was cooled to r.t. and decanted. The supernatant was extracted with ether (3×150 mL.) and the combined organic layers dried over Na2SO4 and evaporated to dryness. The pale yellow residue was stirred with warm 30% ethyl acetate in hexane (200 mL.) and filtered. The title compound (3.5 g.) precipitated from the filtrate upon cooling. MS (M+H)+ 143.2

Workup

  1. customdecanted
  2. extractionThe supernatant was extracted with ether (3×150 mL.)
  3. dry with materialthe combined organic layers dried over Na2SO4
  4. customevaporated to dryness
  5. stirringThe pale yellow residue was stirred
  6. temperaturewith warm 30% ethyl acetate in hexane (200 mL.)
  7. filtrationfiltered
  8. customThe title compound (3.5 g.) precipitated from the filtrate
  9. temperatureupon cooling

Sources & evidence

ORD record
ord-0a545e057bb44b9ebef851e43b536f7c
Source dataset
uspto-grants-2000_05
Patent number
US06069143

Reaction notes

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