Hydrochloric Acid → HCID 15237330, compound

HRID 275401Notes

Reaction equation

HRID 275401 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].[O-]CC.[Na+].Cl[C@@H:22]1[CH2:26][CH2:25][CH2:24][C@H:23]1[S:27][CH2:28][C:29]([OH:31])=[O:30].Cl>C(O)C.O>[CH3:4][C:2]([C:5]1[CH:10]=[C:9]([S:11][C@@H:22]2[CH2:26][CH2:25][CH2:24][C@H:23]2[S:27][CH2:28][C:29]([OH:31])=[O:30])[CH:8]=[C:7]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:6]=1[OH:16])([CH3:1])[CH3:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 703702,6-Di-tert-butyl-4-mercaptophenolHCID 2723922Sodium ethoxideHCID 15237328HCID 15237328, compound

Product 1

HCID 15237330HCID 15237330, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

2.6-bis(1.1-Dimethylethyl)-4-mercaptophenol (0.73 g, 0.0031 mole) was added to freshly prepared sodium ethoxide [sodium (0.16 g, 0,007 mole)] in ethanol (10 ml). Once dissolved, the product of Example 4 (0.50 g, 0.0026 mole) was added and the reaction mixture was stirred for 90 minutes and poured into water (50 ml) containing 1N hydrochloric acid (25 ml). The mixture was extracted three times with 20 ml of diethyl ether, and the combined extracts were washed with water (20 ml), dried over anhydrous magnesium sulfate, filtered and concentrated to an oil with a rotary evaporator. The product was purified by silica gel chromatography. The structure was supported by NMR and elemental analysis.

Workup

  1. dissolutionOnce dissolved
  2. extractionThe mixture was extracted three times with 20 ml of diethyl ether
  3. washthe combined extracts were washed with water (20 ml)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to an oil with a rotary evaporator
  7. customThe product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-422b62fab04044ffaecd1023514b685c
Source dataset
uspto-grants-1995_02
Patent number
US05393764

Reaction notes

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