3-Chloro-4-hydroxybenzoic acid hemihydrate → 3-Chloro-4-hydroxybenzoyl chloride

HRID 236552노트

반응식

HRID 236552 반응식
O.[Cl:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[OH:12])[C:6](O)=[O:7].[Cl:13]C1C=C(C=CC=1O)C(O)=O>S(Cl)(Cl)=O>[Cl:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[OH:12])[C:6]([Cl:13])=[O:7]

참가 물질

3

반응물 1

HCID 27236113-Chloro-4-hydroxybenzoic acid hemihydrate

생성물 1

HCID 202161243-Chloro-4-hydroxybenzoyl chloride

시약·촉매·용매 1

HCID 24386Thionyl Chloride용매

실험 절차

3-Chloro-4-hydroxybenzoic acid hemihydrate (14.5 g.) was heated under reflux for 1 hour with thionyl chloride (80 ml.). The mixture was then evaporated, the residue dissolved in ether and the subsequent solution evaporated. The residue obtained (3-chloro-4-hydroxybenzoyl chloride) was dissolved in ether (80 ml.). The stirred solution was then treated dropwise with a solution of 1,2,3,6-tetrahydropyridine (16.6 g.) in ether (50 ml.) with ice-cooling. The mixture was stirred for 17 hours and evaporated. Water (150 ml.) was then added and the mixture was stirred with ether (50 ml.). The insoluble material was separated by filtration, and combined with the solid obtained by basification of the aqueous phase. The combined solids were stirred with acetone (150 ml.), separated by filtration, washed with acetone (50 ml.) and air-dried to give 1-(3-chloro-4-hydroxybenzoyl)-1,2,3,6-tetrahydropyridine (13.6 g.), m.p. 186°-189° C.

후처리

  1. customThe mixture was then evaporated
  2. dissolutionthe residue dissolved in ether
  3. customthe subsequent solution evaporated

출처 및 근거

ORD 기록
ord-427b664ca99f47cba3b96e12dc62391d
출처 데이터셋
uspto-grants-1987_02
특허 번호
US04645771

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