Hexamethylenetetramine → 2-Hydroxy-4-chloro-5-(1,1-dimethylethyl)benzaldehyde

HRID 1710000

반응식

HRID 1710000 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([OH:12])[CH:5]=[CH:6][C:7]=1[C:8]([CH3:11])([CH3:10])[CH3:9].C1N2CN3CN(C2)CN1C3.FC(F)(F)[C:25](O)=[O:26]>O>[OH:12][C:4]1[CH:3]=[C:2]([Cl:1])[C:7]([C:8]([CH3:9])([CH3:11])[CH3:10])=[CH:6][C:5]=1[CH:25]=[O:26]

참가 물질

5

반응물 3

HCID 4101HexamethylenetetramineHCID 6422Trifluoroacetic acidHCID 134994724-tert-Butyl-3-chlorophenol

생성물 1

HCID 230354272-Hydroxy-4-chloro-5-(1,1-dimethylethyl)benzaldehyde수율 17%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A mixture of 9.65 g (52.2 mmol) of 3-chloro-4-(1,1-dimethylethyl)phenol and 7.37 g (52.2 mmol) of hexamethylenetetramine was refluxed in 150 ml of trifluoroacetic acid for 3 hours. The solution was cooled to ambient temperature and diluted with 500 ml of water. The aqueous residue was extracted with ether. The organic phase was washed with saturated sodium bicarbonate solution, dried and evaporated. The residue was chromatographed on 250 g of silica gel using a gradient from hexane to 20:80 (v/v) ether: hexane as eluent. There was obtained 1.87 g (8.79 mmol, 17%) of 2-hydroxy-4-chloro-5-(1,1-dimethylethyl)benzaldehyde; mp 38°-39° C.

후처리

  1. extractionThe aqueous residue was extracted with ether
  2. washThe organic phase was washed with saturated sodium bicarbonate solution
  3. customdried
  4. customevaporated
  5. customThe residue was chromatographed on 250 g of silica gel using a gradient from hexane to 20:80 (v/v) ether

출처 및 근거

ORD 기록
ord-375129a6d5c34d1b9ba00aca701d145e
출처 데이터셋
uspto-grants-1990_08
특허 번호
US04952583

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