1,2-Ethanedithiol → HCID 9856990, compound

HRID 1007981Notes

Reaction equation

HRID 1007981 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[CH2:14][CH2:13][C:12](=O)[CH2:11][CH2:10]1.[CH2:16]([SH:19])[CH2:17][SH:18].C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[S:18]1[C:12]2([CH2:13][CH2:14][CH:9]([C:3]3[CH:4]=[CH:5][C:6]([OH:8])=[CH:7][C:2]=3[OH:1])[CH2:10][CH2:11]2)[S:19][CH2:16][CH2:17]1

Participants

5

Reactant 3

HCID 109021,2-EthanedithiolHCID 516892Sodium BicarbonateHCID 99424894-(2,4-Dihydroxyphenyl)cyclohexanone

Product 1

HCID 9856990HCID 9856990, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a round bottomed flask equipped with magnetic stirrer was added 4-(2,4-dihydroxyphenyl)cyclohexanone (1 g) and toluene (40 ml). To the stirred solution was added ethane-1,2-dithiol (0.49 ml) and a few crystals of ptoluenesulfonic acid monohydrate and the reaction mixture was heated under reflux for 3.5 hr. The reaction mixture was cooled to room temperature, saturated sodium hydrogencarbonate solution (20 ml) was added, and the layers were separated. The aqueous layer was diluted with water (40 ml) and extracted into ethyl acetate (3×30 ml). The combined organic phases were washed with brine (30 ml), dried over magnesium sulfate, filtered and concentrated in vacuo. Purification via flash chromatography (SiO2, ethyl acetate/petroleum ether 2:3 v/v) furnished the title compound (1.34 g, 98%) as a white solid. δH (CD3OD): 1.59-1.73 (2H, m), 1.75-1.84 (2H, m), 1.98-2.08 (2H, m), 2.14-2.22 (2H, m), 2.77 (1H, tt), 3.22-3.32 (4H, m), 6.18-6.24 (2H, m), 6.85 (1H, d); m/z (ES+) 283 (M+H)+.

Workup

  1. customTo a round bottomed flask equipped with magnetic stirrer
  2. temperatureunder reflux for 3.5 hr
  3. customthe layers were separated
  4. additionThe aqueous layer was diluted with water (40 ml)
  5. extractionextracted into ethyl acetate (3×30 ml)
  6. washThe combined organic phases were washed with brine (30 ml)
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customPurification via flash chromatography (SiO2, ethyl acetate/petroleum ether 2:3 v/v)

Sources & evidence

ORD record
ord-f21fa711f5384d63a4b791bb5923811b
Source dataset
uspto-grants-2004_09
Patent number
US06797731B2

Reaction notes

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