Methanol → HCID 22118423, compound

HRID 1275475Notes

Reaction equation

HRID 1275475 reaction equation
[OH:1][CH2:2][CH:3]1[C:12]2[C:7](=[C:8]([CH3:14])[CH:9]=[CH:10][C:11]=2[CH3:13])[S:6][CH2:5][CH2:4]1.[CH3:15]O.S(=O)(=O)(O)O>CCCCCC.C(OCC)(=O)C>[CH3:15][O:1][CH2:2][CH:3]1[C:12]2[C:7](=[C:8]([CH3:14])[CH:9]=[CH:10][C:11]=2[CH3:13])[S:6][CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 22118392HCID 22118392, compound

Product 1

HCID 22118423HCID 22118423, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

To a mixture of 1.32 g (6.33 mmol) of 4-hydroxymethyl-5,8-dimethylthiochroman with 13 ml of methanol was added 0.1 ml of concentrated sulfuric acid, and the mixture was reacted at reflux under heat for 10 hours. The reaction mixture was cooled to room temperature, poured into ice water and extracted with ethyl acetate. The extract was washed with water and with a saturated sodium chloride aqueous solution. An organic layer was dried over anhydrous sodium sulfate and filtered, and the solvent was distilled off. The residue was purified by column chromatography (silica gel; hexane/ethyl acetate=2/1)to give 0.84 g (yield 60%) of the titled compound.

Workup

  1. customthe mixture was reacted
  2. temperatureat reflux
  3. temperatureunder heat for 10 hours
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with water and with a saturated sodium chloride aqueous solution
  6. dry with materialAn organic layer was dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. distillationthe solvent was distilled off
  9. customThe residue was purified by column chromatography (silica gel

Sources & evidence

ORD record
ord-8339c8812d8d465aaf329b53d17a5185
Source dataset
uspto-grants-2000_12
Patent number
US06159904

Reaction notes

Loading…