Acetic Acid → 2-Oxocyclohexaneheptanoic acid

HRID 1659012Notes

Reaction equation

HRID 1659012 reaction equation
C([C:6]1([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([O-:21])=[O:20])[CH2:11][CH2:10][CH2:9][CH2:8][C:7]1=[O:12])(OCC)=O.S(=O)(=O)(O)O.C(O)(=O)C>O>[C:7]1(=[O:12])[CH2:8][CH2:9][CH2:10][CH2:11][CH:6]1[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 204656027-(2-Carbethoxycyclohexan-1-on-2-yl)heptanoate

Product 1

HCID 204657322-Oxocyclohexaneheptanoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred mixture of 380 g. of mixed methyl and ethyl esters of 7-(2-carbethoxycyclohexan-1-on-2-yl)heptanoate (Example 10), 202 ml. of concentrated sulfuric acid, 970 ml. of glacial acetic acid, and 970 ml. of water is refluxed for 22.5 hours. The cooled reaction mixture is treated with 380 g. of sodium carbonate and 2 liters of water and is extracted with ether. Acidic material is partitioned from the ether extract with 1.0M sodium carbonate. The aqueous phase is acidified with concentrated hydrochloric acid and extracted with ether. The extract is washed successively with water and saturated sodium chloride, dried, and evaporated to give an oil.

Workup

  1. additionA stirred mixture of 380 g
  2. customThe cooled reaction mixture
  3. additionis treated with 380 g
  4. extractionof sodium carbonate and 2 liters of water and is extracted with ether
  5. customAcidic material is partitioned from the ether
  6. extractionextract with 1.0M sodium carbonate
  7. extractionextracted with ether
  8. washThe extract is washed successively with water and saturated sodium chloride
  9. customdried
  10. customevaporated
  11. customto give an oil

Sources & evidence

ORD record
ord-7b4b7d4e5f944e8a93680558e664688a
Source dataset
uspto-grants-1976_06
Patent number
US03966773

Reaction notes

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