Methyl Salicylate → Methyl 2-(oxiran-2-ylmethoxy)benzoate

HRID 1164994ノート

反応式

HRID 1164994 の反応式
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C(=O)([O-])[O-].[K+].[K+].[CH2:18]([CH:20]1[O:22][CH2:21]1)Cl>CC(C)=O>[O:22]1[CH2:21][CH:20]1[CH2:18][O:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

参加物

5

反応物 3

HCID 4133Methyl SalicylateHCID 7835EpichlorohydrinHCID 11430Potassium Carbonate

生成物 1

HCID 279510Methyl 2-(oxiran-2-ylmethoxy)benzoate収率 12%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

A mixture of 15.2 g (0.10 mole) of methyl 2-hydroxybenzoate, 27.6 g (0.20 mole) of potassium carbonate and 31 ml (0.40 mole) of epichlorohydrin in 250 ml of acetone was heated to reflux for 24 hours. The reaction medium was then filtered and evaporated under reduced pressure. The resulting oil was dissolved in 100 ml of toluene and washed consecutively with 100 ml of water, 2×100 ml of 1.0N sodium hydroxide and 2×100 ml of water. The organic phase was then dried over magnesium sulfate and evaporated under reduced pressure to provide the crude product as an oil. Purification was effected by vacuum distillation to provide an oil in 12% yield: boiling point 148° C. (75μ). The NMR and IR spectra and elemental analysis were consistent with the assigned structure.

後処理

  1. temperaturewas heated
  2. temperatureto reflux for 24 hours
  3. filtrationThe reaction medium was then filtered
  4. customevaporated under reduced pressure
  5. dissolutionThe resulting oil was dissolved in 100 ml of toluene
  6. washwashed consecutively with 100 ml of water, 2×100 ml of 1.0N sodium hydroxide and 2×100 ml of water
  7. dry with materialThe organic phase was then dried over magnesium sulfate
  8. customevaporated under reduced pressure

出典と根拠

ORDレコード
ord-3542795e14e844fe944be38958921d65
出典データセット
uspto-grants-1990_03
特許番号
US04906661

反応ノート

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