Dichlorodiphenylmethane → HCID 22475245, compound

HRID 2184112Notes

Reaction equation

HRID 2184112 reaction equation
[Cl:1][C:2]1[C:10]([OH:11])=[C:9]([OH:12])[C:8]([Cl:13])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].Cl[C:15](Cl)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:10]2[O:11][C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[O:12][C:9]=2[C:8]([Cl:13])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 16327DichlorodiphenylmethaneHCID 50914Benzoic acid, dichloro-3,4-dihydroxy-

Product 1

HCID 22475245HCID 22475245, compoundYield 28.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2,5-Dichloro-3,4-dihydroxybenzoic acid (1 g, 4.48 mmol) and dichlorodiphenylmethane (2.12 g, 9.96 mmol) are dissolved in toluene (40 ml) and heated to reflux for 24 hours. After cooling the solvent is evaporated and the residue is purified by column chromatography on silic agel (100 g, dichloromethane then 5% methanol in dichloromethane eluant) to yield the acid as white crystals (490 mg, 28%).

Workup

  1. temperatureheated
  2. temperatureto reflux for 24 hours
  3. temperatureAfter cooling the solvent
  4. customis evaporated
  5. customthe residue is purified by column chromatography on silic agel (100 g, dichloromethane

Sources & evidence

ORD record
ord-843d9724d9a943f5acbb344df2a0f949
Source dataset
uspto-grants-2005_05
Patent number
US06900227B2

Reaction notes

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