Water → Thioxanthene

HRID 581647Notes

Reaction equation

HRID 581647 reaction equation
[CH:1]1[C:14]2[C:13](=O)[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.[H-].[H-].[H-].[H-].[Li+].[Al+3].CCOCC.O>C1C=CC=CC=1>[CH:1]1[C:14]2[CH2:13][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

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 10295ThioxanthoneHCID 21226445Aluminium lithium hydride

Product 1

HCID 67495ThioxantheneYield 98%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of thioxanthone (10 g) in 60 mL of benzene was treated with 5.0 g of LAH by stirring for 15 min. The mixture was heated and 100 mL of ether was added carefully. Reflux was continued for 90 min. The cooled mixture was neutralized with water. The solids were filtered off and the filtrate evaporated to dryness. Pure thioxanthene (9.1 g, 98%) was isolated by chromatography using 20% ethyl acetate/hexane; 1H NMR (CDCl3) δ 3.82 (s, 3H), 7.21 (m, 4H), 7.33 (m, 2H), 7.46 (m, 2H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureReflux
  3. waitwas continued for 90 min
  4. filtrationThe solids were filtered off
  5. customthe filtrate evaporated to dryness

Sources & evidence

ORD record
ord-4a728b20ca324bcdb9d8d56c9eb6c534
Source dataset
uspto-grants-1999_07
Patent number
US05922558

Reaction notes

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