Water → 2,3,5,6-Tetramethyl-1,4-benzenedicarboxylic acid

HRID 467306ノート

反応式

HRID 467306 の反応式
[CH3:1][C:2]1[C:7]([CH3:8])=[C:6]([CH2:9][OH:10])[C:5]([CH3:11])=[C:4]([CH3:12])[C:3]=1[CH2:13][OH:14].S(=O)(=O)(O)[OH:16].[OH2:20]>CC(C)=O.[O-2].[Cr+6].[O-2].[O-2]>[CH3:8][C:7]1[C:2]([CH3:1])=[C:3]([C:13]([OH:14])=[O:20])[C:4]([CH3:12])=[C:5]([CH3:11])[C:6]=1[C:9]([OH:16])=[O:10]

参加物

6

反応物 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 820262,3,5,6-Tetramethyl-1,4-benzenedimethanol

生成物 1

HCID 2615432,3,5,6-Tetramethyl-1,4-benzenedicarboxylic acid収率 80%

試薬・触媒・溶媒 2

HCID 10219390chromium (VI) trioxide触媒HCID 180Acetone溶媒2 回

反応条件

温度
0 °C

実験手順

2,3,5,6-Tetramethyl-p-xylene-α,α'-diol (5.0 g, 26 mmol) was suspended in 250 mL of distilled acetone, and cooled to 0° C. To a separate solution of chromium (VI) oxide (14.15 g, 0.14 ml) in 50 mL of water was dropwise added concentrated sulfuric acid (14.5 mL, 0.26 mol) at 0° C. during 45 minutes. This mixture was then added dropwise during 30 minutes to the acetone solution, with stirring at 0° C. The mixture was stirred vigorously at 0° C. for 1 hour, then at room temperature for 18 hours. The reaction mixture was concentrated by rotary evaporation, and 1NHCl was added to attain pH 1. The product was precipitated by cooling, then was filtered, washed with water (3×) and diethyl ether (3×), and dried at high vacuum to afford 4.55 g (80%) of the product (HOOC--C6 (CH3)4 --COOH) as a white solid, m.p. >300° C.

後処理

  1. stirringThe mixture was stirred vigorously at 0° C. for 1 hour
  2. concentrationThe reaction mixture was concentrated by rotary evaporation, and 1NHCl
  3. additionwas added
  4. customThe product was precipitated
  5. temperatureby cooling
  6. filtrationwas filtered
  7. washwashed with water (3×) and diethyl ether (3×)
  8. customdried at high vacuum

出典と根拠

ORDレコード
ord-2f0ee497d81642419c7f83b70da9eb8d
出典データセット
uspto-grants-1992_10
特許番号
US05158936

反応ノート

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