Cadmium chloride, dihydrate → HCID 178440889, compound

HRID 1388807Notes

Reaction equation

HRID 1388807 reaction equation
[Cl-].[Cd+2:2].[Cl-].Br[C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH:12]([CH3:14])[CH3:13])=[CH:7][CH:6]=1.[Mg]>C1COCC1>[CH2:11]([C:8]1[CH:9]=[CH:10][C:5]([Cd:2][C:5]2[CH:10]=[CH:9][C:8]([CH2:11][CH:12]([CH3:14])[CH3:13])=[CH:7][CH:6]=2)=[CH:6][CH:7]=1)[CH:12]([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 24633Cadmium chloride, dihydrateHCID 37890181-Bromo-4-(2-methylpropyl)benzeneHCID 5462224Magnesium

Product 1

HCID 178440889HCID 178440889, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ten grams of cadmium chloride was added to a Grignard reagent prepared from 21.7 g of p-bromoisobutylbenzene, 2.5 g of magnesium and 400 ml of THF. The mixture was refluxed for 10 minutes to give a solution of di-(p-isobutylphenyl)cadmium. A solution of 18 g of ethyl α-bromopropionate in 20 ml of THF was added to the reaction mixture which had been cooled. After standing at 20° C. for 24 hours, dilute hydrochloric acid was added to the mixture. The mixture was extracted with diethyl ether. The extract was washed with water, dried, concentrated, and purified by silica gel column chromatography to give 4.05 g (17.4%) of ethyl α-(p-isobutylphenyl)propionate.

Workup

  1. temperatureThe mixture was refluxed for 10 minutes

Sources & evidence

ORD record
ord-a81c676f572a4e3abc4fa22338e5824e
Source dataset
uspto-grants-1984_02
Patent number
US04433160

Reaction notes

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