Acetic Acid → 2,4,6,7-Tetramethyl-benzo[1,3]oxathiol-5-ol

HRID 2350978Notes

Reaction equation

HRID 2350978 reaction equation
C([O:4][C:5]1[C:6]([CH3:17])=[C:7]([CH3:16])[C:8]2[O:12][CH:11]([CH3:13])[S:10][C:9]=2[C:14]=1[CH3:15])(=O)C.C[O-].[Na+].O.C(O)(=O)C>CO>[OH:4][C:5]1[C:6]([CH3:17])=[C:7]([CH3:16])[C:8]2[O:12][CH:11]([CH3:13])[S:10][C:9]=2[C:14]=1[CH3:15]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 10942334Sodium MethoxideHCID 13592035HCID 13592035, compound

Product 1

HCID 135920402,4,6,7-Tetramethyl-benzo[1,3]oxathiol-5-olYield 82.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2.9 g of 5-acetoxy-2,4,6,7-tetramethyl-1,3-benzoxathiole, prepared as described in Example 22, were dissolved in 30 ml of methanol, 1.3 g of sodium methoxide was added to the solution, and the mixture was allowed to react at room temperature for 3 hours. At the end of this time, the reaction mixture was poured into water and the solution was neutralized by adding acetic acid. The separated product was extracted with benzene and the extract was washed with water and dried over anhydrous sodium sulfate. The solvent was evaporated off. The crude product thus obtained was purified by silica gel column chromatography. From the fraction eluted with a 1:1 by volume mixture of hexane and benzene were obtained 2.0 g of the title compound, melting at 125°-127° C.

Workup

  1. customto react at room temperature for 3 hours
  2. extractionThe separated product was extracted with benzene
  3. washthe extract was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated off
  6. customThe crude product thus obtained
  7. customwas purified by silica gel column chromatography
  8. washFrom the fraction eluted with a 1:1 by volume mixture of hexane

Sources & evidence

ORD record
ord-89dfbc7bea6c43dbbf59d02cad3c12a8
Source dataset
uspto-grants-1989_10
Patent number
US04871762

Reaction notes

Loading…