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

HRID 1710000

反応式

HRID 1710000 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-375129a6d5c34d1b9ba00aca701d145e
出典データセット
uspto-grants-1990_08
特許番号
US04952583

関連ノート

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