Acetone → HCID 20494745, compound

HRID 1448590Notes

Reaction equation

HRID 1448590 reaction equation
CC(C)=O.C(S)C.[H-].[Na+].[CH3:10][O:11][C:12]1[CH:17]=[C:16]([CH:18]([CH3:26])[CH:19]([CH3:25])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH:15]=[C:14]([O:27]C)[CH:13]=1>O.C1C=CC=CC=1>[CH3:26][CH:18]([C:16]1[CH:17]=[C:12]([O:11][CH3:10])[CH:13]=[C:14]([OH:27])[CH:15]=1)[CH:19]([CH3:25])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

7

Reactant 4

HCID 180AcetoneHCID 6343EthanethiolHCID 24758Sodium hydrideHCID 10611683HCID 10611683, compound

Product 1

HCID 20494745HCID 20494745, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

To 750 ml. cold dimethyl formaldehyde (DMF) was added 100 g. (1.06 mol.) ethanethiol. To this was added slowly 48 g. (1.14 mol.) of 57% NaH in mineral oil (which had been freed of mineral oil by washing with benzene). Then 90 g. (0.34 mol.) 1,3-dimethoxy-5(1,2-dimethylheptyl) benzene was added under a nitrogen atmosphere. The reaction mixture was refluxed overnight. Ice and water (4 l.) was added and the mixture was extracted with ether. The ether extracts were washed twice with 100 ml. 10% H2SO4, twice with water, dried (Na2SO4) and distilled. The product had b.p. 134/0.15 mm n25 =1.5090. Yield 71.5 g. (86%).

Workup

  1. additionTo this was added slowly 48 g
  2. temperatureThe reaction mixture was refluxed overnight
  3. extractionthe mixture was extracted with ether
  4. washThe ether extracts were washed twice with 100 ml
  5. dry with material10% H2SO4, twice with water, dried (Na2SO4)
  6. distillationdistilled

Sources & evidence

ORD record
ord-730817c8e208417884675526564f09bf
Source dataset
uspto-grants-1979_12
Patent number
US04180669

Reaction notes

Loading…