Benzil-di(beta-bromoethyl)ketal → Benzil-di-(beta-hexahydrophthalimidoethyl)ketal

HRID 435179Notes

Reaction equation

HRID 435179 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]([O:20][CH2:21][CH2:22]Br)([C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:13])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[C:24]1(=[O:34])[NH:28][C:27](=[O:29])[CH:26]2[CH2:30][CH2:31][CH2:32][CH2:33][CH:25]12.[Na]>CN(C)C=O>[C:24]1(=[O:34])[N:28]([CH2:2][CH2:3][O:4][C:5]([O:20][CH2:21][CH2:22][N:28]2[C:27](=[O:29])[CH:26]3[CH2:30][CH2:31][CH2:32][CH2:33][CH:25]3[C:24]2=[O:34])([C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:13])[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:27](=[O:29])[CH:26]2[CH2:30][CH2:31][CH2:32][CH2:33][CH:25]12

Participants

4

Reactant 2

HCID 2326685Benzil-di(beta-bromoethyl)ketalHCID 70510219Sodium hexahydrophthalimide

Product 1

HCID 20440913Benzil-di-(beta-hexahydrophthalimidoethyl)ketalYield 91.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Benzil-di-(β-bromoethyl)ketal (13.26 g) and 11.55 g of sodium hexahydrophthalimide were dissolved in 100 ml of N,N-dimethylformamide, and heated at 50° to 60° C. for 5 hours with stirring. The reaction mixture was worked up in the same way as in Example 4 to afford 16.05 g (yield 89.5%) of benzil-di-(β-hexahydrophthalimidoethyl)ketal. Recrystallization from a mixture of ethanol and chloroform afforded crystals having a melting point of 115° to 116° C.

Workup

  1. temperatureheated at 50° to 60° C. for 5 hours

Sources & evidence

ORD record
ord-320dfcd58b36466bbf3c665df3261a5b
Source dataset
uspto-grants-1983_08
Patent number
US04400519

Reaction notes

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