Sulfuric Acid → trans-Ethyl 2-hydroxycyclohexanecarboxylate

HRID 21895

Reaction equation

HRID 21895 reaction equation
[CH3:1][CH2:2][O:3][C:4]([CH:6]1[C:11](=[O:12])[CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5].[BH4-].[Na+].S(=O)(=O)(O)O>C(O)C>[OH:12][C@@H:11]1[CH2:10][CH2:9][CH2:8][CH2:7][C@H:6]1[C:4]([O:3][CH2:2][CH3:1])=[O:5]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 95543Ethyl 2-oxocyclohexanecarboxylateHCID 4311764Sodium borohydride

Product 1

HCID 1268212trans-Ethyl 2-hydroxycyclohexanecarboxylateYield 11.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
0 °C

Procedure

Ethyl cyclohexanone-2-carboxylate (85.0 g, 0.5 mole) was dissolved in ethanol (200 ml) and the solution cooled to 0° C. Sodium borohydride (13.2 g, 0.35 mole) suspended in ethanol (80 ml) was added in small portions whilst the temperature was maintained at below 0° C. After stirring for 2 hours at 0° C. the reaction mixture was made faintly acid by the addition of 50% sulphuric acid and filtered. The filtrate was concentrated in vacuo, taken up in ether and washed with sodium bicarbonate solution. The organic phase was dried over magnesium sulphate and evaporated in vacuo. The residue was chromatographed on silica-gel, eluting initially with 3:1 hexane/ethyl acetate followed by 2:1 hexane/ethyl acetate to give 21.5 g of cis- and 10.0 g of trans-ethyl 2-hydroxycyclohexanecarboxylate.

Workup

  1. additionwas added in small portions whilst the temperature
  2. temperaturewas maintained at below 0° C
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo
  5. washwashed with sodium bicarbonate solution
  6. dry with materialThe organic phase was dried over magnesium sulphate
  7. customevaporated in vacuo
  8. customThe residue was chromatographed on silica-gel
  9. washeluting initially with 3:1 hexane/ethyl acetate

Sources & evidence

ORD record
ord-5cebf6cc66d246d19ec89f9f74c35655
Source dataset
uspto-grants-1995_06
Patent number
US05426090

Linked notes

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