Water → (2,3,4,5-Tetrafluoro-6-methylphenyl)methanol

HRID 1583459

反応式

HRID 1583459 の反応式
[F:1][C:2]1[C:7]([F:8])=[C:6]([F:9])[C:5]([F:10])=[C:4]([CH3:11])[C:3]=1[C:12](O)=[O:13].[H-].[Al+3].[Li+].[H-].[H-].[H-].O>C(OCC)C>[CH3:11][C:4]1[C:5]([F:10])=[C:6]([F:9])[C:7]([F:8])=[C:2]([F:1])[C:3]=1[CH2:12][OH:13]

参加物

5

反応物 3

HCID 962WaterHCID 129439972,3,4,5-Tetrafluoro-6-methylbenzoic acidHCID 21226445Aluminium lithium hydride

生成物 1

HCID 12943998(2,3,4,5-Tetrafluoro-6-methylphenyl)methanol収率 42.9%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

実験手順

3,4,5,6-tetrafluoro-2-toluic acid (500 mg) was dissolved in dry diethyl ether (5.0 ml) added dropwise to a suspension of lithium aluminium hydride (100 mg) in dry ether (10 ml) under an argon atmosphere at the ambient temperature. When the addition was complete and the effervescence has subsided the mixture was heated at the reflux temperature for a period of 1 hour. After allowing the mixture to cool to the ambient temperature water (10 ml) was cautiously added and the resultant mixture extracted with diethyl ether (2×20 ml), the extracts washed with water and dried over anhydrous magnesium sulphate. After filtration the filtrate was concentrated by evaporation of the solvent. The residual low melting solid was recrystallised from petroelum ether (boiling range 40°-60° C.) to yield 2-methyl-3,4,5,6-tetrafluoro-benzyl alcohol (200 mg). N.m.r. ('H(ppm)CDCl3): 2.18(s,1H); 2.32(t,3H); 4.86(s,2H).

後処理

  1. additionWhen the addition
  2. temperaturewas heated at the reflux temperature for a period of 1 hour
  3. additionwas cautiously added
  4. extractionthe resultant mixture extracted with diethyl ether (2×20 ml)
  5. washthe extracts washed with water
  6. dry with materialdried over anhydrous magnesium sulphate
  7. filtrationAfter filtration the filtrate
  8. concentrationwas concentrated by evaporation of the solvent
  9. customThe residual low melting solid was recrystallised from petroelum ether (boiling range 40°-60° C.)

出典と根拠

ORDレコード
ord-56759862cbf5493aa4b3ef8619155cd7
出典データセット
uspto-grants-1985_11
特許番号
US04551546

関連ノート

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