4-Hydroxybenzaldehyde → 4-(2,2,3,3,3-Pentafluoropropoxy)benzaldehyde

HRID 16481

反応式

HRID 16481 の反応式
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].CC1C=CC(S(O[CH2:27][C:28]([F:34])([F:33])[C:29]([F:32])([F:31])[F:30])(=O)=O)=CC=1>CN(C=O)C.C(OCC)(=O)C>[F:33][C:28]([F:34])([C:29]([F:32])([F:31])[F:30])[CH2:27][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 1264-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 27760172,2,3,3,3-Pentafluoropropyl p-Toluenesulfonate

生成物 1

HCID 866134424-(2,2,3,3,3-Pentafluoropropoxy)benzaldehyde収率 30.2%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of 4-hydroxybenzaldehyde (2 g, 16.7 mmol) in DMF (33 mL) was stirred as solid potassium carbonate (4.1 g, 29.7 mmol) was added, and the reaction mixture was then stirred at RT. After 30 min, solid 2,2,3,3,3-pentafluoropropyl 4-methylbenzenesulfonate (5 g, 16.4 mmol) was added into the reaction mixture. The mixture was stirred and heated at 100° C. for 7 h. The reaction mixture was allowed to cool, diluted with ethyl acetate, washed with water (3×) and brine, and concentrated. Purification by flash chromatography on silica gel using a gradient of ethyl acetate in hexane afforded 4-(2,2,3,3,3-pentafluoropropoxy)benzaldehyde (1.26 g).

後処理

  1. additionwas added
  2. stirringThe mixture was stirred
  3. temperatureheated at 100° C. for 7 h
  4. temperatureto cool
  5. washwashed with water (3×) and brine
  6. concentrationconcentrated
  7. customPurification by flash chromatography on silica gel using a gradient of ethyl acetate in hexane

出典と根拠

ORDレコード
ord-6643a3580d464da8982c76918c38200a
出典データセット
uspto-grants-2010_06
特許番号
US07737145B2

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