Sulfuric Acid → 2-Oxocyclopentaneheptanoic acid

HRID 2309558Notes

Reaction equation

HRID 2309558 reaction equation
C([O:3][C:4](=[O:21])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]1(C(OC)=O)[C:15](=[O:16])[CH2:14][CH2:13][CH2:12]1)C.S(=O)(=O)(O)O>O>[O:16]=[C:15]1[CH2:14][CH2:13][CH2:12][CH:11]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][C:4]([OH:21])=[O:3]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 13046296Ethyl-7-(1'-methoxycarbonyl-5-oxocyclopentyl)-heptanoate

Product 1

HCID 989472-Oxocyclopentaneheptanoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of 10.9 g. of ethyl-7-(1'-methoxycarbonyl-5'-oxocyclopentyl)-heptanoate in 100 ml. of distilled water containing 6 g. of conc. sulfuric acid was refluxed under nitrogen. Progress of the reaction was followed by gas chromatography/mass spectroscopy analysis of a sample at intervals. After 48 hours the reaction was virtually complete and the mixture was cooled and extracted with one volume of ethyl ether. The aqueous layer was separated and extracted and extracted again with one volume of ether and the combined ethereal extracts were dried over magnesium sulfate and evaporated to a colorless oil which was sufficiently pure for the next step in the process. Yield was 6.6 g., about 99%.

Workup

  1. additionA suspension of 10.9 g
  2. temperaturethe mixture was cooled
  3. extractionextracted with one volume of ethyl ether
  4. customThe aqueous layer was separated
  5. extractionextracted
  6. extractionextracted again with one volume of ether
  7. dry with materialthe combined ethereal extracts were dried over magnesium sulfate
  8. customevaporated to a colorless oil which

Sources & evidence

ORD record
ord-31e0c47ab56042c0bd659ad271d5b0a2
Source dataset
uspto-grants-1987_09
Patent number
US04695647

Reaction notes

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