Hydrochloric Acid → 1,7-Diphenylheptane-3,5-dione

HRID 1655499Notes

Reaction equation

HRID 1655499 reaction equation
[H-].[Na+].[CH3:3][C:4](=[O:9])[CH2:5][C:6](=[O:8])[CH3:7].CN(C)CCN(C)C.[CH2:18]([Li])[CH2:19][CH2:20][CH3:21].[CH2:23](Cl)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.Cl.[CH2:32]1[CH2:37]CCC[CH2:33]1>>[C:24]1([CH2:23][CH2:3][C:4](=[O:9])[CH2:5][C:6](=[O:8])[CH2:7][CH2:21][C:20]2[CH:37]=[CH:32][CH:33]=[CH:18][CH:19]=2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

8

Reactant 7

HCID 313Hydrochloric AcidHCID 7503Benzyl ChlorideHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 8078Cyclohexane2×HCID 24758Sodium hydrideHCID 31261AcetylacetoneHCID 178418339Butyllithium

Product 1

HCID 101493901,7-Diphenylheptane-3,5-dione

Procedure

To a suspension of sodium hydride (60% in oil, 17 g) in dry cyclohexane (200 ml), a solution of 2,4-pentanedione (37 g, 0.37 mol) in dry cyclohexane was added dropwise at room temperature with stirring under nitrogen, and the resultant mixture was stirred for 40 min at the same temperature. To this suspension, N,N,N',N'-tetramethylethylenediamine (91.8 g) was added dropwise, followed by the dropwise addition of n-butyllithium (1.6M in n-hexane solution, 337 g) at 0° C. or lower and the resultant mixture was stirred for 24 h at room temperature. Then to this suspension, benzyl chloride (93.7 g) was added dropwise at 0°-5° C., stirring was continued for 2 h at room temperature and standed for overnight. The reaction mixture was poured into dilute hydrochloric acid, the organic layer was separated, washed thrice with H2O, dried over MgSO4 and evaporated. The residue (79 g) was distilled under reduced pressure to give the title compound as a pale yellow oil; yield: 23.5 g; bp 185°-190° C./0.4 mmHg.

Workup

  1. stirringstirring
  2. waitstanded for overnight
  3. customthe organic layer was separated
  4. washwashed thrice with H2O
  5. dry with materialdried over MgSO4
  6. customevaporated
  7. distillationThe residue (79 g) was distilled under reduced pressure

Sources & evidence

ORD record
ord-062390df0a944fd0923a9dc793ed023b
Source dataset
uspto-grants-1993_10
Patent number
US05250669

Reaction notes

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