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

HRID 1384319Notes

Reaction equation

HRID 1384319 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

HCID 694522,4-DimethylresorcinolYield 62%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-4599b620827f442494a7e6d7ccaaeacc
Source dataset
uspto-grants-2001_07
Patent number
US06258827B1

Reaction notes

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