1,3-Diacetoxy-2,4-dimethylbenzene → 2,4-Dimethylresorcinol

HRID 1384319노트

반응식

HRID 1384319 반응식
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:10][C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[C:13]([O:18]C(=O)C)[C:12]=1[CH3:22])(=O)C>CCOCC>[OH:10][C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[C:13]([OH:18])[C:12]=1[CH3:22]

참가 물질

4

반응물 2

HCID 211865741,3-Diacetoxy-2,4-dimethylbenzeneHCID 21226445Aluminium lithium hydride

생성물 1

HCID 694522,4-Dimethylresorcinol수율 62%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

To a slurry of lithium aluminum hydride (0.56 g, 14.76 mmol) in ether (35 mL) was added 1,3-diacetoxy-2,4-dimethylbenzene (the compound of Preparation 24, 1.65 g, 7.42 mmol in 40 mL of ether) via syringe. The mixture was stirred overnight; then it was carefully quenched with sodium sulfate decahydrate (excess). The mixture was dried with anhydrous sodium sulfate, filtered, and concentrated to give 0.62 g (62%) of 1,3-dihydroxy-2,4-dimethylbenzene as a waxy light yellow solid which had: NMR δ6.83 (d, J=8 Hz, 1 H), 6.34 (d, J=8.1 Hz, 1 H), 4.71 (s, 2 H), 2.19 (s, 3 H), 2.17 (s, 3 H). There was also a small amount of an impurity observed in the NMR spectrum but the product was found to be suitable for use without further purification. The product was somewhat air sensitive and was used the same day it was synthesized.

후처리

  1. customthen it was carefully quenched with sodium sulfate decahydrate (excess)
  2. dry with materialThe mixture was dried with anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-4599b620827f442494a7e6d7ccaaeacc
출처 데이터셋
uspto-grants-2001_07
특허 번호
US06258827B1

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