Acetone → HCID 54272817, compound

HRID 1979825Notes

Reaction equation

HRID 1979825 reaction equation
[CH3:1][C:2]([CH2:15][CH2:16][CH:17]=[C:18]([CH3:20])[CH3:19])=[CH:3][CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=O)[CH3:13])=[CH:8][CH:7]=1.[CH3:21][CH2:22][O-:23].[Na+].[CH3:25][C:26](C)=[O:27]>>[CH3:1][C:2]([CH2:15][CH2:16][CH:17]=[C:18]([CH3:20])[CH3:19])=[CH:3][CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([CH3:13])=[CH:21][C:22]([O:27][CH2:26][CH3:25])=[O:23])=[CH:8][CH:7]=1

Participants

4

Reactant 3

HCID 180AcetoneHCID 2723922Sodium ethoxideHCID 53734320HCID 53734320, compound

Product 1

HCID 54272817HCID 54272817, compound

Procedure

8 g of p-(4,8-dimethyl-1,3,7-nonatrienyl)acetophenone was added to a solution of 15 g of triethyl phosphonoacetate and 4.2 g of sodium ethylate in 50 ml of dimethylformaldehyde under stirring at room temperature. After stirring at 70° C. for 3 h, the reaction liquid was poured into ice/water, extracted with n-hexane, washed with water and dried over magnesium sulfate. After concentration followed by silica gel column chromatography, 6.1 g of intended ethyl 3-[4-(4,8-dimethyl-1,3,7-nonatrienyl)-phenyl]-2-butenoate was obtained as light yellow crystals.

Workup

  1. stirringAfter stirring at 70° C. for 3 h
  2. customthe reaction liquid
  3. extractionextracted with n-hexane
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationAfter concentration

Sources & evidence

ORD record
ord-b7c995cd29694e47a17fe18421ca7c27
Source dataset
uspto-grants-1984_11
Patent number
US04482734

Reaction notes

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