Hydrochloric Acid → HCID 15524254, compound

HRID 2303967Notes

Reaction equation

HRID 2303967 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([CH2:11][C:12]([O:14][CH3:15])=[O:13])[CH:7]=[CH:8][C:9]=1[Cl:10].Cl[CH2:17][C:18]([O-:20])=[O:19].[Na+].Cl>CS(C)=O>[Cl:3][C:4]1[CH:5]=[C:6]([CH:11]([C:12]([O:14][CH3:15])=[O:13])[CH2:17][C:18]([OH:20])=[O:19])[CH:7]=[CH:8][C:9]=1[Cl:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 1268257Methyl 2-(3,4-dichlorophenyl)acetateHCID 23665759Sodium chloroacetate

Product 1

HCID 15524254HCID 15524254, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

17.94 g of sodium hydride with 61% purity and 350 ml of dried dimethyl sulfoxide were added to a well dried 1-litre 4-necked flask and suspended at room temperature. 99.00 g of methyl 3,4-dichlorophenylacetate was added dropwise thereto under cooling with ice water, the solution being continuously stirred at room temperature even after the end of the dropwise addition. Then 50.38 g of sodium chloroacetate was added under cooling with ice water and the solution was stirred at room temperature. The produced red suspension was poured into a mixture of 500 ml of 1N hydrochloric acid and 300 ml of ice water, and the solution was stirred vigorously. The reaction mixture was extracted with 800 ml of ether, and the organic layer was washed with 500 ml of water (three times) and 500 ml of a saturated saline solution (once). The organic layer was dried over anhydrous sodium sulfate and the solvent was distilled away to obtain 123.94 g of an oily substance. This oily substance was crystallized by treating it with about 400 ml of an ethyl acetate/hexane (1/20) mixture. The precipitated crystals were filtered out, washed with a small quantity of ethyl acetate/hexane (1/20) and then dried to give 93.46 g of the primary crystals of the title substance. Meanwhile, the filtrate was concentrated and crystallized from ethyl acetate/hexane, and the precipitated crystals were filtered out and dried to obtain 9.29 g of the secondary crystals (102.75 g with the primary and secondary crystals put together, 81.0% yield) of the title substance.

Workup

  1. customsuspended at room temperature
  2. additioneven after the end of the dropwise addition
  3. stirringthe solution was stirred at room temperature
  4. stirringthe solution was stirred vigorously
  5. extractionThe reaction mixture was extracted with 800 ml of ether
  6. washthe organic layer was washed with 500 ml of water (three times) and 500 ml of a saturated saline solution (once)
  7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  8. distillationthe solvent was distilled away
  9. customto obtain 123.94 g of an oily substance
  10. customThis oily substance was crystallized
  11. additionby treating it with about 400 ml of an ethyl acetate/hexane (1/20) mixture
  12. filtrationThe precipitated crystals were filtered out
  13. washwashed with a small quantity of ethyl acetate/hexane (1/20)
  14. customdried

Sources & evidence

ORD record
ord-8c06e213465848b9ac58d30f331daa53
Source dataset
uspto-grants-2002_08
Patent number
US06433174B1

Reaction notes

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