Isopropanol → Ethyl 4-oxocyclohexanecarboxylate

HRID 704584Notes

Reaction equation

HRID 704584 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.OC1CCC(C(OCC)=O)CC1.[Cr](O)(O)(=O)=O.C(O)(C)C>CC(C)=O>[O:1]=[C:2]1[CH2:12][CH2:11][CH:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 8434EthylparabenHCID 24425Chromic AcidHCID 86973Ethyl 4-hydroxycyclohexanecarboxylate

Product 1

HCID 317638Ethyl 4-oxocyclohexanecarboxylate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl 4-hydroxybenzoate is reduced to ethyl 4-hydroxycyclohexanecarboxylate according to the procedure described in R. A. Finnegan and P. L. Bachman, Journal of Organic Chemistry, Volume 30, pages 4145-4150 (1965). The crude material obtained in this reduction (190 g) is dissolved in 1200 ml of reagent grade acetone. The solution is cooled to 0° C. and 152 ml of a 8 N chromic acid solution (prepared from concentrated sulfuric acid and chromium trioxide) is added dropwise to the mechanically stirred reaction mixture. Enough isopropanol is added to the mixture to discharge its red color and it is then filtered through Celite. The salts are washed with several portions of acetone. The filtrate is evaporated in vacuo. The residue is dissolved in 750 ml of diethyl ether and washed with sodium bicarbonate and brine solutions. After drying, the solvent is evaporated and the residue is distilled to yield the title compound; bp12 125 ° C.

Workup

  1. customThe crude material obtained in this reduction (190 g)
  2. filtrationis then filtered through Celite
  3. washThe salts are washed with several portions of acetone
  4. customThe filtrate is evaporated in vacuo
  5. dissolutionThe residue is dissolved in 750 ml of diethyl ether
  6. washwashed with sodium bicarbonate and brine solutions
  7. customAfter drying
  8. customthe solvent is evaporated
  9. distillationthe residue is distilled

Sources & evidence

ORD record
ord-9d2f61070bd24a54863587cd2cc0c9be
Source dataset
uspto-grants-1991_01
Patent number
US04988699

Reaction notes

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