Methanol → HCID 14145816, compound

HRID 1704748Notes

Reaction equation

HRID 1704748 reaction equation
[CH3:1][S:2]([CH:4]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[O:6][C:5]1=O)=O.C[OH:16]>Cl>[CH3:1][S:2][C:4]1[C:13](=[O:16])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[O:6][CH:5]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 22758705HCID 22758705, compound

Product 1

HCID 14145816HCID 14145816, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent2×

Procedure

A mixture of 3-(methylsulfinyl)chromanone (11 g), methanol (100 ml) and 1N hydrochloric acid (100 ml) is stirred at room temperature for 20 hrs. The methanol is removed at reduced pressure, and the aqueous residue is extracted with chloroform. The chloroform extracts are combined, extracted with 1N sodium hydroxide solution, washed with water, dried over MgSO4 and evaporated to give an oil. The oil is heated at 100° C. in 5N hydrochloric acid (100 ml) for 5 hrs. The solution is cooled, and the product which precipitated is filtered off. Recrystallization from methanol gives 3-(methylthio)chromone (2) as white crystals (7.2 g, 72%), mp 103°-105° C.

Workup

  1. customThe methanol is removed at reduced pressure
  2. extractionthe aqueous residue is extracted with chloroform
  3. extractionextracted with 1N sodium hydroxide solution
  4. washwashed with water
  5. dry with materialdried over MgSO4
  6. customevaporated
  7. customto give an oil
  8. temperatureThe solution is cooled
  9. customthe product which precipitated
  10. filtrationis filtered off
  11. customRecrystallization from methanol

Sources & evidence

ORD record
ord-46a7c4a03d854b0b9bcf080ce549947e
Source dataset
uspto-grants-1978_11
Patent number
US04127669

Reaction notes

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