HCID 12525860, compound → HCID 12525863, compound

HRID 441667Notes

Reaction equation

HRID 441667 reaction equation
[CH3:1][O:2][C:3]1[CH:22]=[CH:21][C:6](/[CH:7]=[CH:8]/[C:9]2[C:10]([C:18]([OH:20])=[O:19])=[CH:11][CH:12]=[C:13]([C:15]([OH:17])=[O:16])[CH:14]=2)=[CH:5][CH:4]=1>CN(C)C=O.C(O)(=O)C.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][CH2:8][C:9]2[CH:14]=[C:13]([C:15]([OH:17])=[O:16])[CH:12]=[CH:11][C:10]=2[C:18]([OH:20])=[O:19])=[CH:21][CH:22]=1

Participants

5

Reactant 1

HCID 12525860HCID 12525860, compound

Product 1

HCID 12525863HCID 12525863, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

45 G. of a mixture of 3-(p-methoxybenzylidene)phthalide-5- and -6- carboxylic acids, obtained by the condensation of p-methoxyphenylacetic acid and benzene-1,2,4-tricarboxylic anhydride as described in Example 1, was hydrogenated for 20 hours in 250 ml of dimethylformamide containing 10.5 g. of 10% palladium on carbon catalyst. The solution was filtered and the filtrate evaporated. The residue was recrystallized from aqueous acetic acid to afford 3-(p-methoxybenzyl)phthalide-5- and -6- carboxylic acids. 24.1 G of this mixture was dissolved in 90 ml of dimethylsulfoxide and 30 g. of potassium tertbutoxide was added. After 15 minutes the solution was poured into water, acidified with acetic acid, and the product filtered off. Fractional crystallization from dioxan afforded 4'-methoxy-trans-stilbene 2,4-dicarboxylic acid as the less soluble isomer, and 4'-methoxy-trans-stilbene-2,5-dicarboxylic acid as the more soluble isomer. 2.4 G. of 4'-methoxy-trans-stilbene-2,5-dicarboxylic acid was hydrogenated for 41/2 hours in 20 ml dimethylformamide and 20 ml of acetic acid containing 0.3 g. of 10% palladium on carbon catalyst. The solution was filtered and evaporated and the residue recrystallized from aqueous ethanol to afford 2-(4-methoxyphenethyl)benzene-1,4-dicarboxylic acid. This compound was then cyclized by the procedure of part A of this example to give 2-carboxy-7-methoxy-10,11-dihydro-5-oxo-5H-dibenzo[a,d]cycloheptene having a m.p. of 201°-203° C.

Workup

  1. filtrationThe solution was filtered
  2. customevaporated
  3. customthe residue recrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-b247c29097c044f58ad8d825a6d4ccdf
Source dataset
uspto-grants-1977_08
Patent number
US04041173

Reaction notes

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