Acetophenone → 1,3-Octanedione, 4-ethyl-1-phenyl-

HRID 1585270Notes

Reaction equation

HRID 1585270 reaction equation
[H-].[Na+].[C:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)(=[O:5])[CH3:4].[CH2:12]([CH:14]([CH2:19][CH2:20][CH2:21][CH3:22])[C:15](OC)=[O:16])[CH3:13]>C1(C)C(C)=CC=CC=1>[CH3:22][CH2:21][CH2:20][CH2:19][CH:14]([C:15]([CH2:4][C:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5])=[O:16])[CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 7410Acetophenone2×HCID 24758Sodium hydrideHCID 102491Methyl 2-ethylhexanoate

Product 1

HCID 111183501,3-Octanedione, 4-ethyl-1-phenyl-Yield 81%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent2×

Procedure

The conditions of Example 1 were repeated except that the following amounts were used: 60% sodium hydride in mineral oil (200 g, 5.03 mol. 2.0 mol/mol acetophenone), methyl 2-ethylhexanoate (618 g, 3.91 mol, 1.5 mol/mol acetophenone), xylene (449 g), and then a solution of acetophenone (304 g, 2.53 mol) in xylene (180 g) was added over 1 h. The mixture was kept at reflux for an additional 30 min. Workup of the reaction mixture gave material having product in a crude yield of 89%. Vacuum distillation (200 mtorr) through a 15 cm Vigreux column yielded the product in the heart cut: 4-ethyl-1-phenyl-1,3-octadione (523 g, 97% pure, 2.06 mol; 81% yield; bp: 128-169° C.). Dypnone was undetectable in the product.

Workup

  1. temperatureat reflux for an additional 30 min
  2. customWorkup of the reaction mixture gave material
  3. distillationVacuum distillation (200 mtorr) through a 15 cm Vigreux column
  4. customyielded the product in the heart cut

Sources & evidence

ORD record
ord-84853d796961440f84e3c4532c37bb3f
Source dataset
uspto-grants-1999_08
Patent number
US05936129

Reaction notes

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