Hydrochloric Acid → 2,2-Dimethoxycarbonyl-5-chloroindane

HRID 1633395Notes

Reaction equation

HRID 1633395 reaction equation
C[O-].[Na+].[Na].Br[CH2:6][C:7]1[C:8]([CH2:14]Br)=[CH:9][C:10]([Cl:13])=[CH:11][CH:12]=1.[C:16]([O:23][CH3:24])(=[O:22])[CH2:17][C:18]([O:20][CH3:21])=[O:19].Cl>CCOCC.CO>[CH3:21][O:20][C:18]([C:17]1([C:16]([O:23][CH3:24])=[O:22])[CH2:14][C:8]2[C:7](=[CH:12][CH:11]=[C:10]([Cl:13])[CH:9]=2)[CH2:6]1)=[O:19]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7943Dimethyl malonateHCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 150082261,2-Bis(bromomethyl)-4-chlorobenzene

Product 1

HCID 204410142,2-Dimethoxycarbonyl-5-chloroindaneYield 95.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 3283Diethyl EtherSolvent2×

Procedure

To a methanol solution of sodium methylate prepared from 16.04 g of sodium metal and 250 ml of methanol, with ice-cooling, was added a solution of 110.6 g of α,α'-dibromo-4-chloro-o-xylene in 100 ml of anhydrous ether. To the mixture, was added slowly a solution of 46.02 g of dimethyl malonate in 50 ml of anhydrous ether. The mixture was stirred for 48 hours at room temperature to complete the reaction. The reaction mixture was poured into a mixture of 100 ml of 1% aqueous hydrochloric acid solution and ice, and extracted with ether. The aqueous layer was extracted twice with ether. The ether layers were combined, washed with saturated aqueous sodium hydrogencarbonate solution, then with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain 89.4 g of the intended product.

Workup

  1. temperaturecooling
  2. customthe reaction
  3. extractionextracted with ether
  4. extractionThe aqueous layer was extracted twice with ether
  5. washwashed with saturated aqueous sodium hydrogencarbonate solution
  6. dry with materialwith saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-918ab7d840e64f878a9182201e1f6ac0
Source dataset
uspto-grants-1984_10
Patent number
US04480118

Reaction notes

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