Benzyl Chloride → 4-Benzyloxy-6-methyl-2H-pyran-2-one

HRID 2909

Reaction equation

HRID 2909 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7](Cl)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[OH:15][C:16]1[CH:21]=[C:20]([CH3:22])[O:19][C:18](=[O:23])[CH:17]=1.C1OCCOCCOCCOCCOCCOC1>CN(C)C=O>[CH2:7]([O:15][C:16]1[CH:21]=[C:20]([CH3:22])[O:19][C:18](=[O:23])[CH:17]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 546757574-Hydroxy-6-methyl-2-pyrone

Product 1

HCID 27844494-Benzyloxy-6-methyl-2H-pyran-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

124.4 g (0.900 mol) potassium carbonate and 63 ml (0.547 mol) benzyl chloride were added in succession to a solution of 56.7 g (0.450 mol) 4-hydroxy-6-methyl-2H-pyran-2-one and 1.0 g (0.004 mol) 18-crown-6 in 900 ml anhydrous dimethyl-formamide. It was stirred vigorously for 4.5 hours at an internal temperature of 70°-75° C. It was suction filtered and the residue was washed well with ethyl acetate. The combined filtrates were extensively evaporated in a vacuum and subsequently poured onto ice water. The aspirated precipitate was recrystallized from t-butylmethyl ether after drying. 69.0 g (71%) V, melting point 92°-93° C.

Workup

  1. filtrationfiltered
  2. washthe residue was washed well with ethyl acetate
  3. customThe combined filtrates were extensively evaporated in a vacuum
  4. additionsubsequently poured onto ice water
  5. customThe aspirated precipitate was recrystallized from t-butylmethyl ether
  6. customafter drying

Sources & evidence

ORD record
ord-9faac40bc60f4f9481fb3e21ace77f7b
Source dataset
uspto-grants-1998_03
Patent number
US05731344

Linked notes

Loading…