Pyridine → 1-(Benzyloxy)-2-(chloromethyl)benzene

HRID 256413

反応式

HRID 256413 の反応式
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=1[CH2:11]O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.OC1C=CC=CC=1CO.C([Cl:33])C1C=CC=CC=1.CC(C)([O-])C.[K+].N1C=CC=CC=1.S(Cl)(Cl)=O>C(O)C.C(Cl)(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=1[CH2:11][Cl:33])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

9

反応物 6

HCID 1049PyridineHCID 5146Salicyl AlcoholHCID 7503Benzyl ChlorideHCID 18811Benzenemethanol, 2-(phenylmethoxy)-HCID 24386Thionyl ChlorideHCID 23665647Potassium tert-butoxide

生成物 1

HCID 5635071-(Benzyloxy)-2-(chloromethyl)benzene収率 81%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 6212Chloroform溶媒2 回

実験手順

To a solution of 46.5 (0.217 mole) 2-benzyloxybenzyl alcohol (prepared by reaction of 2-hydroxybenzyl alcohol with benzyl chloride in ethanol containing an equimolar amount of potassium t-butoxide at 100° C.) in 100 ml chloroform was added 17.2 g (0.217 mole) pyridine followed by dropwise addition of a solution of 25.8 g (0.217 mole) thionyl chloride in 60 ml chloroform. The resulting mixture was heated at reflux for 1.5 hours, cooled, washed with water, brine and dried (MgSO4). Evaporation of solvent gave 45.8 g crude oil which was distilled in vacuo to yield 40.7 g (81%) of product as a colorless oil, b.p. 141° C.(1 Torr).

後処理

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 1.5 hours
  3. temperaturecooled
  4. washwashed with water, brine
  5. dry with materialdried (MgSO4)
  6. customEvaporation of solvent
  7. customgave 45.8 g crude oil which
  8. distillationwas distilled in vacuo

出典と根拠

ORDレコード
ord-e57e3edb022740a8926893137e99290e
出典データセット
uspto-grants-1987_10
特許番号
US04703052

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