Hydrochloric Acid → HCID 18466563, compound

HRID 2229146Notes

Reaction equation

HRID 2229146 reaction equation
[H-].[Na+].[CH3:3][S:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:7][CH:6]=1.Cl.[CH:18](OCC)=[O:19]>>[CH3:3][S:4][C:5]1[CH:6]=[CH:7][C:8]([CH:11]([CH:18]=[O:19])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:9][CH:10]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 8025Ethyl formateHCID 24758Sodium hydrideHCID 10512649Ethyl [4-(methylsulfanyl)phenyl]acetate

Product 1

HCID 18466563HCID 18466563, compound

Procedure

A suspension of NaH (0.84 g, 20.8 mmol) was added at room temperature to a solution of ethyl 4-methylthiophenylacetate (1.1 g, 5.2 mmol) in ethyl formate (20 mL). The mixture was stirred at room temperature for 1 hour and then cold 0.5 N HCl (20 mL) was added slowly. The crude reaction was then extracted with ether, and the organic layer was washed with sodium bicarbonate, brine, dried over magnesium sulfate, filtered, and concentrated to yield 1.2 g of ethyl 4-methylthio-α-formyl-phenylacetate as a colorless oil, which was used in the next step without purification.

Workup

  1. customThe crude reaction
  2. extractionwas then extracted with ether
  3. washthe organic layer was washed with sodium bicarbonate, brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d7279effab2c4cc2b2585698274f20c2
Source dataset
uspto-grants-2002_07
Patent number
US06420349B1

Reaction notes

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