Hydrochloric Acid → HCID 15287672, compound

HRID 1885929Notes

Reaction equation

HRID 1885929 reaction equation
[CH3:1][C:2]([C:5]1[CH:10]=[C:9]([SH:11])[CH:8]=[CH:7][C:6]=1[OH:12])([CH3:4])[CH3:3].C[O-].[Na+].[CH:16]12[O:21][CH:17]1[CH2:18][CH2:19][CH2:20]2.Cl>CO.[Cl-].[Na+].O.O>[CH3:1][C:2]([C:7]1[CH:8]=[C:9]([S:11][C@@H:20]2[CH2:19][CH2:18][CH2:17][C@H:16]2[OH:21])[CH:10]=[C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[C:6]=1[OH:12])([CH3:4])[CH3:3]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 92446-Oxabicyclo[3.1.0]hexaneHCID 10942334Sodium MethoxideHCID 15540416HCID 15540416, compound

Product 1

HCID 15287672HCID 15287672, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

2.6-bis(1,1-Dimethylethyl-4- mercaptophenol (11.5 g, 0.048 mole) was added to a solution of sodium methoxide [prepared from sodium (2.2 g, 0.097 mole)] in methanol (75 ml). After several minutes, cyclopentene oxide (3.86 g, 0.046 mole) was added, and the reaction mixture was stirred at room temperature for 20 hours. The reaction mixture was poured into water (100 ml) containing saturated brine (50 ml) and 1N hydrochloric acid (80 ml). The mixture was extracted twice with 100 ml of diethyl ether. The combined diethyl ether extracts were dried over anhydrous magnesium sulfate, filtered and concentrated to an oil with a rotary evaporator. The product was purified by silica gel chromatography to give the product as a white solid which was recrystallized from hexane (DSC.m.p. 90° C.). The structure was supported by NMR and elemental analysis. Analysis calculated for: C19H30SO2 (m.w.=322.50): Theory: C, 70.76; H, 9.38; S, 9.94. Found: C, 71.14; H, 9.64; S, 10.02.

Workup

  1. waitAfter several minutes
  2. extractionThe mixture was extracted twice with 100 ml of diethyl ether
  3. dry with materialThe combined diethyl ether extracts were dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to an oil with a rotary evaporator
  6. customThe product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-3cd40ed86d984890b1ae9dda35f33e51
Source dataset
uspto-grants-1992_09
Patent number
US05147893

Reaction notes

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