Dichlorodiphenylmethane → Methyl 4,7-dichloro-2,2-diphenyl-1,3-benzodioxol-5-carboxylate

HRID 1755877Notes

Reaction equation

HRID 1755877 reaction equation
[Cl:1][C:2]1[C:11]([OH:12])=[C:10]([OH:13])[C:9]([Cl:14])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].Cl[C:16](Cl)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>>[Cl:1][C:2]1[C:11]2[O:12][C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[O:13][C:10]=2[C:9]([Cl:14])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

3

Reactant 2

HCID 16327DichlorodiphenylmethaneHCID 19917975Methyl 2,5-dichloro-3,4-dihydroxybenzoate

Product 1

HCID 19917882Methyl 4,7-dichloro-2,2-diphenyl-1,3-benzodioxol-5-carboxylateYield 70.4%

Procedure

Methyl 2,5-dichloro-3,4-dihydroxybenzoate (1.1 g) (about 4.6 mmol) and 2.0 g (8.4 mmol) of dichlorodiphenylmethane are heated together to 150° C. After stirring for 1.5 hours the melt is cooled and the product is crystallized from diethyl ether. There are obtained 1.3 g of methyl 4,7-dichloro-2,2-diphenyl-1,3-benzodioxol-5-carboxylate as white crystals of m.p. 112° C.

Workup

  1. temperatureis cooled
  2. customthe product is crystallized from diethyl ether

Sources & evidence

ORD record
ord-dca0e9fa3bb4456aa544e79ff7a576ab
Source dataset
uspto-grants-1995_08
Patent number
US05438052

Reaction notes

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