Oxygen → Methyl cyclohex-1-ene-1-carboxylate

HRID 1413223ノート

反応式

HRID 1413223 の反応式
C1(C(O)C(Cl)(Cl)Cl)CCCC=C1.O=O.[Na].[CH:16]1([C:22]([O:24][CH3:25])=[O:23])[CH2:21][CH2:20][CH2:19][CH:18]=[CH:17]1>CO.O.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1>[C:16]1([C:22]([O:24][CH3:25])=[O:23])[CH2:21][CH2:20][CH2:19][CH2:18][CH:17]=1

参加物

7

反応物 4

HCID 977OxygenHCID 5360545SodiumHCID 11007985Methyl cyclohex-2-ene-1-carboxylateHCID 12418397HCID 12418397、化合物

生成物 1

HCID 87647Methyl cyclohex-1-ene-1-carboxylate収率 59%

試薬・触媒・溶媒 2

HCID 212261,10-Phenanthroline hydrate触媒2 回HCID 887Methanol溶媒3 回

実験手順

1-(2-Cyclohexen-1-yl)-2,2,2-trichloroethanol (20 g; 87.3 m. moles) was added to a solution of cupric chloride dihydrate (0.25 g; 1.47 m. moles) and a 1,10-phenanthroline hydrate (0.75 g; 3.8 m. moles) in methanol (150 ml). A rapid stream of oxygen was passed through the vigorously stirred solution and a solution of sodium (2.5 g; 108.5 m. moles) in methanol (50 ml) was added over a period of 41/4 hours. A solution of cupric chloride dihydrate (0.125 g; 0.733 m. moles) and 1,10-phenanthroline hydrate (0.375 g; 1.9 m. moles) in methanol (10 ml) was then added and the reaction allowed to proceed for a further 11/4 hours at a temperature of 20°-25° C. The reaction mixture was poured into ice-cold dilute hydrochloric acid, extracted with ether (4×100 ml) and the combined extracts washed twice with dilute aqueous sodium carbonate. The dried (MgSO4) extract was evaporated and the residue distilled to give a mixture of methyl 2-cyclohexene-1-carboxylate and methyl 1-cyclohexene-1-carboxylate (7.2 g; yield 59%), b.p. 80°-85° C./12 mm, containing about 90% of the former as indicated by G.L.C.

後処理

  1. custom4 hours
  2. customat a temperature of 20°-25° C
  3. additionThe reaction mixture was poured into ice-cold dilute hydrochloric acid
  4. extractionextracted with ether (4×100 ml)
  5. washthe combined extracts washed twice with dilute aqueous sodium carbonate
  6. dry with materialThe dried (MgSO4)
  7. extractionextract
  8. customwas evaporated
  9. distillationthe residue distilled
  10. customto give

出典と根拠

ORDレコード
ord-458a6342f00d405ca12bfc5fd7bcc3d7
出典データセット
uspto-grants-1981_02
特許番号
US04249015

反応ノート

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