4-Hydroxybenzaldehyde → 4-(2,2,2-Trifluoroethoxy)benzaldehyde

HRID 456279

反応式

HRID 456279 の反応式
[H-].[Na+].[OH:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1.CC1C=CC(S(O[CH2:23][C:24]([F:27])([F:26])[F:25])(=O)=O)=CC=1.O>CN(C=O)C.C(OCC)(=O)C>[F:25][C:24]([F:27])([F:26])[CH2:23][O:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1

参加物

7

反応物 4

HCID 1264-HydroxybenzaldehydeHCID 962WaterHCID 24758Sodium hydrideHCID 67942Ethanol, 2,2,2-trifluoro-, 1-(4-methylbenzenesulfonate)

生成物 1

HCID 47709464-(2,2,2-Trifluoroethoxy)benzaldehyde収率 42%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒3 回HCID 8857Ethyl Acetate溶媒2 回

実験手順

Sodium hydride (787 mg, 55%, 18.0 mmol) was suspended in DMF (10 mL) under a nitrogen atmosphere, and a solution of DMF (5 mL) containing 4-hydroxybenzaldehyde (2.00 g, 16.4 mmol) was dropwise added thereto over 5 minutes at room temperature. A light yellow insoluble substance was precipitated immediately after the addition. After 5 minutes, a solution of DMF (5 mL) containing 2,2,2-trifluoroethyl 4-methylbenzenesulfonate (4.00 g, 17.2 mmol) was added dropwise thereto to give a brown solution. This brown solution was stirred at room temperature for 1 hour, and then water (100 mL) and ethyl acetate (150 mL) were added thereto. The organic layer was separated, further washed with water (50 mL) five times, with a 10% sodium hydroxide aqueous solution (50 mL) three times, and with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated to give a crude product. This crude product was purified by silica gel column chromatography (hexane:ethyl acetate, 5:1, v/v) to give 1.40 g of the title compound (light yellow oil, yield: 42%).

後処理

  1. additionwas dropwise added
  2. customA light yellow insoluble substance was precipitated immediately
  3. additionafter the addition
  4. waitAfter 5 minutes
  5. additionwas added dropwise
  6. customto give a brown solution
  7. customThe organic layer was separated
  8. washfurther washed with water (50 mL) five times, with a 10% sodium hydroxide aqueous solution (50 mL) three times
  9. dry with materialwith saturated brine, and dried over anhydrous magnesium sulfate
  10. customThe solvent was evaporated
  11. customto give a crude product
  12. customThis crude product was purified by silica gel column chromatography (hexane

出典と根拠

ORDレコード
ord-c79dd6ff01864d94a297c3d6d4f0dfe0
出典データセット
uspto-grants-2013_07
特許番号
US08497397B2

関連ノート

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