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

HRID 1779274Notes

Reaction equation

HRID 1779274 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 mole) 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 hours at room temperature. Then to this suspension, benzyl chloride (93.7 g) was added dropwise at 0°-5° C., stirring was continued for 2 hours at room temperature and allowed to stand overnight. The reaction mixture was poured into dilute hydrochloric acid. The organic layer was separated, washed thrice with H2O, dried over anhydrous MgSO4 and evaporated. The residue (79 g) was distilled under reduced pressure to give 23.5 g of the desired product as a pale yellow oil having a boiling point of 185°-190° C./0.4 mmHg.

Workup

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

Sources & evidence

ORD record
ord-19a4a55187cc4294be997fb779bd68e6
Source dataset
uspto-grants-1997_05
Patent number
US05627006

Reaction notes

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