Potassium Hydroxide → HCID 54419678, compound

HRID 280292Notes

Reaction equation

HRID 280292 reaction equation
[OH-].[K+].[Cl:3][C:4]1[CH:5]=[C:6]([CH:19]=[CH:20][CH:21]=1)[CH2:7][CH:8]([C:14]([O:16]CC)=[O:15])[C:9]([O:11][CH2:12][CH3:13])=[O:10]>C(O)C>[CH2:12]([O:11][C:9](=[O:10])[CH:8]([CH2:7][C:6]1[CH:19]=[CH:20][CH:21]=[C:4]([Cl:3])[CH:5]=1)[C:14]([OH:16])=[O:15])[CH3:13]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 10803022HCID 10803022, compound

Product 1

HCID 54419678HCID 54419678, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of potassium hydroxide (26 g) in absolute ethanol (375 ml) is added during 30 minutes to an ice-cold solution of diethyl 3-chlorobenzylmalonate (112 g) in absolute ethanol (375 ml). The solution is stirred at room temperature for 18 hours, and the solvent removed under reduced pressure. The residue is dissolved in water (1200 ml) and the solution cooled in an ice-bath. Concentrated hydrochloric acid (29 ml) is added, and the solution extracted with ether (2×350 ml). The combined ether solutions are washed with water (250 ml), dried over magnesium sulfate, and evaporated under reduced pressure to give as an oil, 3-chlorobenzylmalonic acid monoethyl ester; NMR (CDCl3)δ: 10.13 (s, 1H), 7.2 (m, 4H), 4.15 (q, 2H), 3.5 (m, 3H), 1.21 (t, 3H).

Workup

  1. customthe solvent removed under reduced pressure
  2. dissolutionThe residue is dissolved in water (1200 ml)
  3. temperaturethe solution cooled in an ice-bath
  4. additionConcentrated hydrochloric acid (29 ml) is added
  5. extractionthe solution extracted with ether (2×350 ml)
  6. washThe combined ether solutions are washed with water (250 ml)
  7. dry with materialdried over magnesium sulfate
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-276a95686dce46bcbef9976305f03743
Source dataset
uspto-grants-1986_05
Patent number
US04588746

Reaction notes

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