Formaldehyde → 3,3-Bis(hydroxymethyl)-2,3-dihydro-4H-1-benzothiopyran-4-one

HRID 1009211Notes

Reaction equation

HRID 1009211 reaction equation
[S:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[CH2:3][CH2:2]1.[CH2:12]=[O:13].[C:14](=[O:17])([O-])[O-].[K+].[K+]>CO.O>[OH:13][CH2:12][C:3]1([CH2:14][OH:17])[C:4](=[O:11])[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[S:1][CH2:2]1

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 11430Potassium CarbonateHCID 19048Thiochroman-4-one

Product 1

HCID 27640233,3-Bis(hydroxymethyl)-2,3-dihydro-4H-1-benzothiopyran-4-one

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

A solution of thiochroman-4-one (2.0 g, 12 mmol) in MeOH (40 ml) and water (8 ml) was admixed with 35% eq. formalin solution (8 ml) and potassium carbonate (200 mg). The reaction mixture was stirred at 40° C. for 2 h and then at RT for 2 h, the solvent was removed under reduced pressure and the residue was admixed with water. The aqueous solution was extracted repeatedly with EtOAc, the combined organic phases were dried over sodium sulfate and the solvent was removed under reduced pressure. After column chromatography purification of the residue (silica gel, 1:1 cyclohexane/EtOAc), the desired product was obtained as a white solid (1.71 g, 63% of theory, m.p. 136-139° C.).

Workup

  1. waitat RT for 2 h
  2. customthe solvent was removed under reduced pressure
  3. extractionThe aqueous solution was extracted repeatedly with EtOAc
  4. dry with materialthe combined organic phases were dried over sodium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customAfter column chromatography purification of the residue (silica gel, 1:1 cyclohexane/EtOAc)

Sources & evidence

ORD record
ord-237e216f9c534e61a207f2d196d474de
Source dataset
uspto-grants-2011_07
Patent number
US07973072B2

Reaction notes

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