Benzyl Alcohol → Phenylmethyl 4-methyl-3-oxopentanoate

HRID 1099588Notes

Reaction equation

HRID 1099588 reaction equation
[C:1]([CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])(=[O:5])[CH:2]([CH3:4])[CH3:3].C(O)[C:13]1[CH:18]=[CH:17]C=[CH:15][CH:14]=1>C1(C)C=CC=CC=1>[CH3:3][CH:2]([CH3:4])[C:1](=[O:5])[CH2:6][C:7]([O:9][CH2:10][C:11]1[CH:17]=[CH:18][CH:13]=[CH:14][CH:15]=1)=[O:8]

Participants

4

Reactant 2

HCID 244Benzyl AlcoholHCID 81583Ethyl isobutyrylacetate

Product 1

HCID 11276044Phenylmethyl 4-methyl-3-oxopentanoate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3 g of molecular sieve (4 Å) were activated in a microwave oven at 100 W for 5 min. The molecular sieve obtained in this manner was then initially charged, and 200 ml of anhydrous toluene were added. 4.9 g (30.97 mmol) of ethyl isobutyrylacetate and 4.02 g (37.2 mmol) of benzyl alcohol were then added. The reaction mixture was heated at reflux temperature for 6 h. After cooling, the molecular sieve was filtered off and the solvent was distilled off under reduced pressure. The residue was chromatographed on silica gel (mobile phase: cyclohexane/ethyl acetate 10/1). This gave 4.70 g (65% of theory) of the target compound.

Workup

  1. customThe molecular sieve obtained in this manner
  2. additionwas then initially charged
  3. temperatureThe reaction mixture was heated
  4. temperatureat reflux temperature for 6 h
  5. temperatureAfter cooling
  6. filtrationthe molecular sieve was filtered off
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was chromatographed on silica gel (mobile phase: cyclohexane/ethyl acetate 10/1)

Sources & evidence

ORD record
ord-d54ab16b80ea4a979bd10ed4f57be92d
Source dataset
uspto-grants-2012_03
Patent number
US08143411B2

Reaction notes

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