Sulfuric Acid → trans-Ethyl 2-hydroxycyclohexanecarboxylate

HRID 21895

반응식

HRID 21895 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 1268212trans-Ethyl 2-hydroxycyclohexanecarboxylate수율 11.6%

시약·촉매·용매 1

HCID 702Ethanol용매2회

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5cebf6cc66d246d19ec89f9f74c35655
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05426090

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