Hydrochloric Acid → HCID 86746141, compound

HRID 1741692Notes

Reaction equation

HRID 1741692 reaction equation
[CH3:1][C:2]([C:5]1[CH:10]=[C:9]([SH:11])[CH:8]=[C:7]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:6]=1[OH:16])([CH3:4])[CH3:3].Cl[CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]1[S:24]([CH2:27][C:28]([O:30][CH3:31])=[O:29])(=[O:26])=[O:25].Cl>C(N(CC)CC)C>[CH3:4][C:2]([C:5]1[CH:10]=[C:9]([S:11][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]2[S:24]([CH2:27][C:28]([O:30][CH3:31])=[O:29])(=[O:26])=[O:25])[CH:8]=[C:7]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:6]=1[OH:16])([CH3:1])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 703702,6-Di-tert-butyl-4-mercaptophenolHCID 54174524HCID 54174524, compound

Product 1

HCID 86746141HCID 86746141, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

2,6-bis(1,1-Dimethylethyl)-4-mercaptophenol (3.2 g, 0.013 mole) was added to a solution of methyl [(2-chlorocyclohexyl)sulfonyl]acetate (0.85 g, 0.0033 mole) in triethylamine (13 ml) and the reaction mixture was refluxed for 5 hours. The reaction mixture was cooled to room temperature and poured into 1 N hydrochloric acid (150 ml). The mixture was extracted twice with 50 ml of diethyl ether, then washed twice with 20 ml of 1.5 N hydrochloric acid and once with brine (10 ml), dried over anhydrous magnesium sulfate, filtered and concentrated in a rotary evaporator to give the crude product as an oil. The product was purified by silica gel chromatography to give a solid m.p. ca. 105° C. The structure was supported by NMR, and infrared spectroscopy and elemental analysis.

Workup

  1. temperaturethe reaction mixture was refluxed for 5 hours
  2. extractionThe mixture was extracted twice with 50 ml of diethyl ether
  3. washwashed twice with 20 ml of 1.5 N hydrochloric acid and once with brine (10 ml)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in a rotary evaporator
  7. customto give the crude product as an oil
  8. customThe product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-86838edb36bb4e53bafc2a7c8233207b
Source dataset
uspto-grants-1994_08
Patent number
US05334616

Reaction notes

Loading…