Chloroacetone → HCID 19925664, compound

HRID 1647497Notes

Reaction equation

HRID 1647497 reaction equation
[C:1]([C:5]1[CH:12]=[C:9]([CH:10]=O)[C:8]([OH:13])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:21][C:22](=[O:24])[CH3:23]>C(#N)C>[C:22]([C:23]1[O:13][C:8]2[CH:7]=[CH:6][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:12][C:9]=2[CH:10]=1)(=[O:24])[CH3:21]

Participants

5

Reactant 3

HCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 14750905-tert-Butylsalicylaldehyde

Product 1

HCID 19925664HCID 19925664, compoundYield 60.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5-tert-Butylsalicylaldehyde (163 g) was dissolved in 1.5 liters of acetonitrile, 252.5 g of anhydrous potassium carbonate was added and 84.6 g of chloroacetone was dropped into the mixture with stirring at room temperature. After completion of the dropping, the reaction mixture was stirred for 8 hours and then insoluble matters were filtered off. The filtrate was concentrated in vacuo and the residue was dissolved in ethyl acetate followed by washing with water twice. The ethyl acetate layer was dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was crystallized by adding isopropyl ether thereto followed by filtering to give 120.5 g of crystals. M.p. 99°-101° C.

Workup

  1. stirringAfter completion of the dropping, the reaction mixture was stirred for 8 hours
  2. filtrationinsoluble matters were filtered off
  3. concentrationThe filtrate was concentrated in vacuo
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washby washing with water twice
  6. dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was crystallized
  9. additionby adding isopropyl ether
  10. filtrationby filtering

Sources & evidence

ORD record
ord-c21de757b81643a5aa7e8d8778c6ef18
Source dataset
uspto-grants-1995_07
Patent number
US05432195

Reaction notes

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