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

HRID 467306노트

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HRID 467306 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 10219390chromium (VI) trioxide촉매HCID 180Acetone용매2회

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온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-2f0ee497d81642419c7f83b70da9eb8d
출처 데이터셋
uspto-grants-1992_10
특허 번호
US05158936

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