Toluene → Nonyl-3,4-epoxycylohexanecarboxylate

HRID 640027

反応式

HRID 640027 の反応式
[CH2:1]([OH:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[O:11]1[CH:17]2[CH:12]1[CH2:13][CH:14]([C:18](OC)=[O:19])[CH2:15][CH2:16]2.N12CCN(CC1)CC2.C1(C)C=CC=CC=1>CO>[CH2:1]([O:10][C:18]([CH:14]1[CH2:15][CH2:16][CH:17]2[O:11][CH:12]2[CH2:13]1)=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

参加物

6

反応物 4

HCID 1140TolueneHCID 89141-NonanolHCID 9237DabcoHCID 127701647-Oxabicyclo[4.1.0]heptane-3-carboxylic acid, methyl ester

生成物 1

HCID 58671997Nonyl-3,4-epoxycylohexanecarboxylate

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a 3-neck 250 mL flask equipped with an argon inlet, stir bar and distillation apparatus was added 1-nonanol (19.99 g, 0.14 mol, obtained from Sigma-Aldrich), methyl 3,4-epoxycyclohexanecarboxylate (ERL-4140, 23.80 g, 0.15 mol, obtained from Dow Chemical Company), 1,4-diazabicyclo[2.2.2]octane (DABCO™, 3.96 g, 35 mmol, obtained from Sigma-Aldrich) and toluene (60 mL). The reaction mixture was refluxed until methanol ceased collecting in the receiving flask and the completion of the reaction was confirmed by 1H NMR spectroscopy. The still pot from the distillation was diluted with toluene (60 mL) and washed with brine (3×60 mL). The organic layer was separated, dried over MgSO4 and filtered. The solvent was removed in vacuo. The excess methyl 3,4-epoxycyclohexane carboxylate was removed via Kugelrohr distillation under reduced vacuum to give 33.39 g (90%) of a clear, colorless oil of nonyl-3,4-epoxycylohexanecarboxylate 1H NMR (CDCl3, δ): 4.06 (td, J=6.7, 1.9 Hz, 2H), 3.25-3.10 (m, 2H), 2.55-2.42 (m, 1H), 2.31-1.27 (m, 20H), 0.88 (t, J=6.7 Hz, 3H).

後処理

  1. customTo a 3-neck 250 mL flask equipped with an argon inlet
  2. distillationdistillation apparatus
  3. customceased collecting in the receiving flask
  4. distillationThe still pot from the distillation
  5. additionwas diluted with toluene (60 mL)
  6. washwashed with brine (3×60 mL)
  7. customThe organic layer was separated
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customThe solvent was removed in vacuo
  11. customThe excess methyl 3,4-epoxycyclohexane carboxylate was removed via Kugelrohr distillation under reduced vacuum

出典と根拠

ORDレコード
ord-96ef5e1a649146c99c69fa6cb5f0040b
出典データセット
uspto-grants-2010_04
特許番号
US07691920B2

関連ノート

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