Hydrochloric Acid → 3-(4-Chlorophenyl)-3-oxopropanal

HRID 1941705Notes

Reaction equation

HRID 1941705 reaction equation
[CH:1](OCC)=[O:2].[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:15])[CH3:14])=[CH:9][CH:8]=1.C[O-].[Na+].Cl>CCOCC>[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:15])[CH2:14][CH:1]=[O:2])=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7467P-ChloroacetophenoneHCID 8025Ethyl formateHCID 10942334Sodium Methoxide

Product 1

HCID 104423563-(4-Chlorophenyl)-3-oxopropanalYield 100.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Ethyl formate (8.15 g, 0.11 mol) and 4′-chloroacetophenone (15.4 g, 0.1 mol) were stirred in ether (150 mL) at room temperature. Sodium methoxide (25%) (23.77 g, 0.11 mol) was added dropwise. The mixture was stirred at room temperature for 16 hours and was then treated with 150 mL of 1N hydrochloric acid. The phases were separated and the ethereal solution washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo to afford 18.3 g of a yellow oil. The resulting crude mixture was used directly in the next step without purification.

Workup

  1. customThe phases were separated
  2. washthe ethereal solution washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9b9dc4fd40474022806e97056924a4ff
Source dataset
uspto-grants-2013_03
Patent number
USRE044048E1

Reaction notes

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