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

HRID 256413

반응식

HRID 256413 반응식
[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

참가 물질

9

반응물 6

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

생성물 1

HCID 5635071-(Benzyloxy)-2-(chloromethyl)benzene수율 81%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 6212Chloroform용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-e57e3edb022740a8926893137e99290e
출처 데이터셋
uspto-grants-1987_10
특허 번호
US04703052

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