Potassium Iodide → Methyl 12-Methyl-12H-dibenzo[d,g][1,3]dioxocin-6-carboxylate

HRID 359189Notes

Reaction equation

HRID 359189 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[OH:16])[CH3:9].Cl[CH:18](Cl)[C:19]([OH:21])=[O:20].[C:23](=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(O)(C)C.CO>[CH3:9][CH:8]1[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][CH:18]([C:19]([O:21][CH3:23])=[O:20])[O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]1=2

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 6597Dichloroacetic AcidHCID 11430Potassium CarbonateHCID 13530914Ethylidenebisphenol

Product 1

HCID 14839712Methyl 12-Methyl-12H-dibenzo[d,g][1,3]dioxocin-6-carboxylate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3776IsopropanolSolvent

Procedure

1,1-Bis(2-hydroxyphenyl)ethane was treated with dichloroacetic acid, potassium carbonate, and potassium iodide in isopropyl alcohol as in Example 3 and the product obtained was esterified with methanol as in Example 4 to obtain 1.71 g of the title compound as a mixture of cis and trans isomers. A portion of this was recrystallized from ether to obtain a pure sample of the cis isomer of the title compound as a white solid melting at 146°-147° C. The geometry was determined by proton NMR spectroscopy.

Workup

  1. customthe product obtained

Sources & evidence

ORD record
ord-a3720385f4284d2ab232a24c86e9fb7d
Source dataset
uspto-grants-1991_03
Patent number
US04999448

Reaction notes

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