Dichlorodiphenylmethane → HCID 19756157, compound

HRID 1587720Notes

Reaction equation

HRID 1587720 reaction equation
[OH:1][C:2]1[C:3]([OH:13])=[C:4]2[C:9](=[O:10])[NH:8][C:6](=[O:7])[C:5]2=[CH:11][CH:12]=1.[C:14]1([C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)(Cl)Cl)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>>[C:14]1([C:20]2([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[O:1][C:2]3[C:3](=[C:4]4[C:9](=[O:10])[NH:8][C:6](=[O:7])[C:5]4=[CH:11][CH:12]=3)[O:13]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

3

Reactant 2

HCID 16327DichlorodiphenylmethaneHCID 166409824,5-dihydroxy-2,3-dihydro-1H-isoindole-1,3-dione

Product 1

HCID 19756157HCID 19756157, compound

Conditions

Temperature
160 °C

Procedure

A suspension of the dihydroxyphthalimide from e) (350 mg) in diphenyldichloromethane (4 g) was heated at 160° C. for 3 hours. The resultant solution was cooled and washed with petroleum ether (3×10 ml). The petrol phase separated to give a brown oil which was collected and triturated under diethyl ether (5 ml) to give as a chestnut brown solid, diphenylmethylenedioxyphthalimide (300 mg); NMR (DMSO-d6) 7.5(m,12H); 11.05(s,1H). Cooling of the petrol phase afforded a second fraction of the phthalimide (250 mg).

Workup

  1. washwashed with petroleum ether (3×10 ml)
  2. customThe petrol phase separated
  3. customto give a brown oil which
  4. customwas collected
  5. customtriturated under diethyl ether (5 ml)

Sources & evidence

ORD record
ord-c7d60c508fe14f23a4bdda970d01bccd
Source dataset
uspto-grants-1993_06
Patent number
US05219848

Reaction notes

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