Dimethylformamide → 2,6-Dichloro-4-methylbenzoyl chloride

HRID 280649노트

반응식

HRID 280649 반응식
[Cl:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]([Cl:12])[C:3]=1[C:4](O)=[O:5].CN(C)C=O.S(Cl)([Cl:20])=O>>[Cl:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]([Cl:12])[C:3]=1[C:4]([Cl:20])=[O:5]

참가 물질

4

반응물 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 136496822,6-Dichloro-4-methylbenzoic acid

생성물 1

HCID 150651842,6-Dichloro-4-methylbenzoyl chloride수율 109%

실험 절차

A solution of 2,6-dichloro-4methylbenzoic acid (7.15 g, 34.9 mmol) in thionyl chloride (133 ml) containing dimethylformamide (1.3 ml) was refluxed 3 hours, evaporated under vacuum, and azeotroped twice with benzene. The residue was triturated with petroleum ether (b.p. 30°-60° C., 200 ml) and filtered. The filtrate was evaporated under vacuum to provide 8.5 g (109% of theory) 2,6-dichloro-4-methylbenzoyl chloride, IR (neat): 1785 cm-1. The crude chloride and chlorobenzene (94 g) were stirred in carbon tetrachloride (235 ml), treated in portions with aluminum chloride (5.35 g, 40.1 mmol), kept 30 minutes at ambient temperature, and refluxed 3 hours. The mixture was cooled, quenched by addition of ice and concentrated hydrochloric acid, and extracted three times with dichloromethane. The combined extracts were washed with water, dried over anhydrous magnesium sulfate, and evaporated under vacuum. The residue was chromatographed on a column of silica gel (400 g) eluted with 3:2 (v/v) dichloromethane-hexane to provide 7.19 g (69%) of 4-(4-chlorobenzoyl)-3,5-dichlorotoluene, m.p. 111.5°-114° C.

후처리

  1. temperaturewas refluxed 3 hours
  2. customevaporated under vacuum
  3. customazeotroped twice with benzene
  4. customThe residue was triturated with petroleum ether (b.p. 30°-60° C., 200 ml)
  5. filtrationfiltered
  6. customThe filtrate was evaporated under vacuum

출처 및 근거

ORD 기록
ord-0ba9ff48635c43d2af16db0b3fc42bc5
출처 데이터셋
uspto-grants-1986_05
특허 번호
US04590201

반응 노트

불러오는 중…