4-Methylbenzenethiol → 9,10-Anthracenedione, 1,5-bis[(4-methylphenyl)thio]-

HRID 1726840Notes

Reaction equation

HRID 1726840 reaction equation
BrC1C=CC(O[C:7]2[C:20]3[C:19](=[O:21])[C:18]4[C:13](=[C:14](OC5C=CC(Br)=CC=5)[CH:15]=[CH:16][CH:17]=4)[C:12](=[O:30])[C:11]=3[CH:10]=[CH:9][CH:8]=2)=CC=1.[OH-].[K+].[C:35]1([CH3:42])[CH:40]=[CH:39][C:38]([SH:41])=[CH:37][CH:36]=1>CN(C=O)C>[CH3:42][C:35]1[CH:40]=[CH:39][C:38]([S:41][C:7]2[C:20]3[C:19](=[O:21])[C:18]4[C:13](=[C:14]([S:41][C:38]5[CH:39]=[CH:40][C:35]([CH3:42])=[CH:36][CH:37]=5)[CH:15]=[CH:16][CH:17]=4)[C:12](=[O:30])[C:11]=3[CH:10]=[CH:9][CH:8]=2)=[CH:37][CH:36]=1

Participants

5

Reactant 3

HCID 78114-MethylbenzenethiolHCID 14797Potassium HydroxideHCID 23089718HCID 23089718, compound

Product 1

HCID 110049109,10-Anthracenedione, 1,5-bis[(4-methylphenyl)thio]-

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

10 parts of 1,5-bis(4-bromophenoxy)anthraquinone, 8 parts of potassium hydroxide, and 9 parts of 4-toluenethiol were added to 100 parts of DMF, and the mixture was stirred under heat at 110° C. for 3 hours. The precipitated solid after cooling was filtered, washed, and dried, to give 6.5 parts of an intermediate (1,5-bis(4-methylphenylthio)anthraquinone).

Workup

  1. temperatureThe precipitated solid after cooling
  2. filtrationwas filtered
  3. washwashed
  4. customdried

Sources & evidence

ORD record
ord-57b215f0d0b544e98ff9045f0bddba0f
Source dataset
uspto-grants-2009_02
Patent number
US07494721B2

Reaction notes

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