Thionyl Chloride → Anthraquinone-2-carbonyl Chloride

HRID 1636199

Reaction equation

HRID 1636199 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)[C:6](=[O:16])[C:5]=2[CH:4]=[CH:3][C:2]=1[C:17]([OH:19])=O.S(Cl)([Cl:22])=O>ClCCl>[CH:1]1[C:14]2[C:13](=[O:15])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6](=[O:16])[C:5]=2[CH:4]=[CH:3][C:2]=1[C:17]([Cl:22])=[O:19]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 670302-Anthraquinonecarboxylic acid

Product 1

HCID 15025286Anthraquinone-2-carbonyl Chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Anthraquinone-2-carboxylic acid (2.52 g, 10 mmol) was suspended in dichloro methane (100 ml). Thionyl chloride (50 ml) was added and the mixture heated to reflux in a nitrogen atmosphere for several hours giving a clear yellow solution. Dichloro methane and excess thionyl chloride was removed in vacuo giving a yellow solid. The solid was filtered off, washed several times with petroleum ether and dried in vacuo. Yield 2.69 g (99% from anthraquinone-2-carboxylic acid); MP: 143-144.5° C.; TLC (analyzed as the methyl ester: a small sample of the acid chloride was dissolved in dry methanol and analyzed immediately using ethyl acetate as eluent); Rf =0.68. MS (FAB+): 307.1 (MH+).

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux in a nitrogen atmosphere for several hours
  3. customgiving a clear yellow solution
  4. customDichloro methane and excess thionyl chloride was removed in vacuo
  5. customgiving a yellow solid
  6. filtrationThe solid was filtered off
  7. washwashed several times with petroleum ether
  8. customdried in vacuo
  9. dissolutiona small sample of the acid chloride was dissolved in dry methanol

Sources & evidence

ORD record
ord-f33fec283bf24b3ba13503f2623c2424
Source dataset
uspto-grants-2000_03
Patent number
US06033784

Linked notes

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