Hydrochloric Acid → HCID 13103759, compound

HRID 354685Notes

Reaction equation

HRID 354685 reaction equation
[CH3:1][O:2][C:3]1[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[CH:17][C:4]=1[CH2:5][CH:6]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:7]([O:9][CH2:10][CH3:11])=[O:8].[H-].[Na+].[Cl:27]N1C(=O)CCC1=O.Cl>O1CCCC1.O>[Cl:27][C:6]([CH2:5][C:4]1[CH:17]=[C:18]([O:23][CH3:24])[C:19]([O:21][CH3:22])=[CH:20][C:3]=1[O:2][CH3:1])([C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 31398ChlorosuccinimideHCID 13103753Diethyl 2,4,5-trimethoxybenzylmalonate

Product 1

HCID 13103759HCID 13103759, compoundYield 91.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

In 70 ml of anhydrous tetrahydrofuran is dissolved 6.5 g of diethyl 2,4,5-trimethoxybenzylmalonate and, then, 760 mg of 60% oily sodium hydride is added. The mixture is stirred at room temperature for 15 minutes, after which time 2.54 g of N-chlorosuccinimide is added. The mixture is further stirred at room temperature for 30 minutes. The reaction mixture is poured into a mixture of 300 ml water and 10 ml 6N-HCl and, then, extracted with ether. The ethereal layer is washed with water, dried (over MgSO4) and distilled to remove the ether, whereupon 6.5 g (91.5%) of diethyl α-chloro-α-(2,4,5-trimethoxybenzyl)malonate is obtained as crystals melting at 84°-85° C.

Workup

  1. stirringThe mixture is further stirred at room temperature for 30 minutes
  2. extractionextracted with ether
  3. washThe ethereal layer is washed with water
  4. dry with materialdried (over MgSO4)
  5. distillationdistilled
  6. customto remove the ether

Sources & evidence

ORD record
ord-906a4fdce16a4e0aaf9d3ce3b45d2b50
Source dataset
uspto-grants-1983_03
Patent number
US04376777

Reaction notes

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