Hydrochloric Acid → HCID 13174739, compound

HRID 1870780Notes

Reaction equation

HRID 1870780 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:6][CH:5]=1.[CH:16](OCC)=[O:17].Cl>O1CCCC1>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([CH:10]([CH:16]=[O:17])[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8025Ethyl formateHCID 24758Sodium hydrideHCID 84177Ethyl (4-chlorophenyl)acetate

Product 1

HCID 13174739HCID 13174739, compoundYield 78.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Then, 4.19 g of sodium hydride (60% in oil) was suspended in 150 ml of tetrahydrofuran, to which a solution of 19.0 g of ethyl 4-chlorophenylacetate in 150 ml of tetrahydrofuran was added dropwise at 5° to 10° C. After stirring at room temperature for 1.5 hours, 8.42 g of ethyl formate was added, and the mixture was further stirred at room temperature for 4.5 hours. After completion of the reaction, the reaction mixture was cooled to ice temperature, neutralized by the addition of diluted hydrochloric acid, and concentrated. The residue was subjected to phase separation with ethyl acetate-water, and the organic layer was dried and then concentrated. The residue was subjected to silica gel chromatography, which afforded 17.0 g of ethyl 2-(4'-chlorophenyl)-2-formylacetate.

Workup

  1. additionwas added dropwise at 5° to 10° C
  2. stirringthe mixture was further stirred at room temperature for 4.5 hours
  3. customAfter completion of the reaction
  4. temperaturethe reaction mixture was cooled to ice temperature
  5. concentrationconcentrated
  6. customThe residue was subjected to phase separation with ethyl acetate-water
  7. customthe organic layer was dried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-1a828f135bd146e3926270c8b92e0d9f
Source dataset
uspto-grants-2000_08
Patent number
US06100257

Reaction notes

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