Dimethyl Sulfoxide → 1-Phenyl-1,3-octadecanedione

HRID 2225986Notes

Reaction equation

HRID 2225986 reaction equation
CS(C)=O.[C:5]([O:22]C)(=O)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].[C:24]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)(=[O:26])[CH3:25]>O1CCCC1>[C:27]1([C:24](=[O:26])[CH2:25][C:5](=[O:22])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 7410AcetophenoneHCID 8181Methyl Palmitate

Product 1

HCID 870271-Phenyl-1,3-octadecanedione

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

An apparatus as described in Example 1 is charged with 31.7 g of sodium-tert-butylate, 150 g of DMSO and 150 g of tetrahydrofuran (THF) and the mixture is cooled to 0° C. Then a mixture of 89 g of methyl palmitate and 36 g of acetophenone is added dropwise over 45 minutes. The reaction mixture is then stirred for ca. 45-60 minutes at 30° C., the solvent is removed by distillation on a rotary evaporator (bath temperature <60° C.), and the residue is taken up in 1000 ml of water. The aqueous solution is acidified with dilute hydrochloric acid and the precipitate is isolated by filtration, washed with water, and dried.

Workup

  1. additionis added dropwise over 45 minutes
  2. customthe solvent is removed by distillation on a rotary evaporator (bath temperature <60° C.)
  3. customthe precipitate is isolated by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-68a0561f4e754eecb677d9c6c44c67e8
Source dataset
uspto-grants-1994_09
Patent number
US05344992

Reaction notes

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