Sulfuric Acid → trans-Ethyl 2-hydroxycyclohexanecarboxylate

HRID 21895

反応式

HRID 21895 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 1268212trans-Ethyl 2-hydroxycyclohexanecarboxylate収率 11.6%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒2 回

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-5cebf6cc66d246d19ec89f9f74c35655
出典データセット
uspto-grants-1995_06
特許番号
US05426090

関連ノート

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