Thionyl Chloride → HCID 13948363, compound

HRID 1899836Notes

Reaction equation

HRID 1899836 reaction equation
O[CH2:2][CH:3]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:4]([O:6][CH2:7][CH3:8])=[O:5].O=S(Cl)[Cl:17].C(=O)(O)[O-].[Na+]>ClCCl>[Cl:17][CH2:2][CH:3]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 596249HCID 596249, compound

Product 1

HCID 13948363HCID 13948363, compoundYield 45.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To ethyl 3-hydroxy-2-phenylpropionate (2.55 g, 13.1 mmol) in dichloromethane (15 ml), SOCl2 (1.87 g, 15.7 mmol) in dichloromethane (1 ml) was added while chilling with ice. After the resulting solution was stirred to cause reaction at room temperature for 3 hours, saturated aqueous sodium bicarbonate was added while chilling with ice. The prepared solution was extracted with dichloromethane, and the extract was washed with saturated aqueous sodium chloride, and then dried over anhydrous sodium sulfate. Subsequently, the solvent was removed by distillation under reduced pressure to obtain a crude product. The product was purified by silica gel column chromatography using acetone/hexane=1/3 to obtain 1.27 g of the titled compound as a colorless oil (yield: 45.5%).

Workup

  1. temperaturewhile chilling with ice
  2. customreaction at room temperature for 3 hours
  3. temperaturewhile chilling with ice
  4. extractionThe prepared solution was extracted with dichloromethane
  5. washthe extract was washed with saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. customSubsequently, the solvent was removed by distillation under reduced pressure
  8. customto obtain a crude product
  9. customThe product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c35dfb848abe47fda8b96cbf7881f648
Source dataset
uspto-grants-1996_11
Patent number
US05574030

Reaction notes

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