Thioxanthone → 9H-thioxanthen-9-ol

HRID 393259

Reaction equation

HRID 393259 reaction equation
[CH:1]1[C:14]2[C:13](=[O:15])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[S:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+]>CO>[CH:11]1[C:12]2[CH:13]([OH:15])[C:14]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[S:6][C:7]=2[CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 10295ThioxanthoneHCID 4311764Sodium borohydride

Product 1

HCID 51541709H-thioxanthen-9-olYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of thioxanthen-9-one [31] (2 g, 9.42 mmol) in anhydrous CH3OH (30 mL) was stirred under N2 and NaBH4 (1.42 g, 37.68 mmol) was added slowly in portions over 15 min. After complete addition the reaction mixture was heated at reflux (3 hr.) and cooled to room temperature. Ice-water was added and the reaction mixture was extracted with CH2Cl2 (3×50 mL). The combined CH2Cl2 extracts were washed with water, brine, dried (MgSO4). The solvent was removed under reduced pressure to give a yellow solid, which was recrystallized from pet.ether to give 1.87 g (93%) of the alcohol as pale yellow needles, mp 104-105° C.

Workup

  1. additionAfter complete addition the reaction mixture
  2. temperaturewas heated
  3. temperatureat reflux (3 hr.)
  4. extractionthe reaction mixture was extracted with CH2Cl2 (3×50 mL)
  5. washThe combined CH2Cl2 extracts were washed with water, brine
  6. dry with materialdried (MgSO4)
  7. customThe solvent was removed under reduced pressure
  8. customto give a yellow solid, which
  9. customwas recrystallized from pet

Sources & evidence

ORD record
ord-5a0f4c1e54344c8ca6ce20442184321b
Source dataset
uspto-grants-2004_10
Patent number
US06806283B2

Linked notes

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