Lithium hydride → HCID 3007321, compound

HRID 426788Notes

Reaction equation

HRID 426788 reaction equation
[CH3:1][CH2:2][C:3](=[O:9])[CH2:4][C:5](=[O:8])[CH2:6][CH3:7].[H-].[Li+].I[CH2:13][CH2:14][CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][CH2:26]I)=[CH:19][CH:18]=1>CN(C)C=O>[C:5]([CH:4]([C:3](=[O:9])[CH2:2][CH3:1])[CH2:13][CH2:14][CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][CH2:26][CH:4]([C:3](=[O:9])[CH2:2][CH3:1])[C:5](=[O:8])[CH2:6][CH3:7])=[CH:19][CH:18]=1)(=[O:8])[CH2:6][CH3:7]

Participants

5

Reactant 3

HCID 62714Lithium hydrideHCID 819233,5-HeptanedioneHCID 20333111HCID 20333111, compound

Product 1

HCID 3007321HCID 3007321, compoundYield 15.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 16.1 g (0.126 m) of 3,5-heptanedione in 50 ml of dimethylformamide was added during 15 minutes to a stirred suspension of 1.2 g of lithium hydride in 100 ml of dimethylformamide. The mixture was stirred one hour at room temperature and then a solution of 27.6 g (0.0619 m) of 1,4-bis(3-iodopropyloxy)benzene in 100 ml of dimethylformaide was added. The reaction mixture was heated at 60°-70° C. for about 16 hours and then concentrated in vacuo. The residue was distilled to remove volatiles (150° C., 0.05 mm) and chromatographed on 400 g of silica with chloroform:acetonitrile 95:5. The product was distilled at 250° C. (0.02 mm) and crystallized from ether to give 4.4 g of 1,4-bis(4,4-dipropionylbutyloxy)benzene, m.p. 57°-58° C.

Workup

  1. temperatureThe reaction mixture was heated at 60°-70° C. for about 16 hours
  2. concentrationconcentrated in vacuo
  3. distillationThe residue was distilled
  4. customto remove volatiles (150° C., 0.05 mm)
  5. customchromatographed on 400 g of silica with chloroform:acetonitrile 95:5
  6. distillationThe product was distilled at 250° C. (0.02 mm)
  7. customcrystallized from ether

Sources & evidence

ORD record
ord-3b524297e30e496b8ef8cfb2638c8fb2
Source dataset
uspto-grants-1979_10
Patent number
US04171365

Reaction notes

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