Hydrochloric Acid → HCID 86746141, compound

HRID 1885940Notes

Reaction equation

HRID 1885940 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 1N hydrochloric acid (150 ml). The mixture was extracted twice with 50 ml of diethyl ether, then washed twice with 20 ml of 1.5N 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 1.5N 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-631a0dbc13c644d88b4090ff93af48c8
Source dataset
uspto-grants-1992_09
Patent number
US05147893

Reaction notes

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