trans-2,3-Dimethyloxirane → 2,6-Bis(1,1-dimethylethyl)-4-[(2-hydroxy-1-methylpropyl)thio]phenol

HRID 845083Notes

Reaction equation

HRID 845083 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+].[Na].[CH3:22][C@@H:23]1[O:25][C@H:24]1[CH3:26]>C(O)C>[CH3:13][C:12]([C:7]1[CH:8]=[C:9]([S:11][CH:23]([CH3:22])[CH:24]([OH:25])[CH3:26])[CH:10]=[C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[C:6]=1[OH:16])([CH3:15])[CH3:14]

Participants

6

Reactant 4

HCID 30664trans-2,3-DimethyloxiraneHCID 703702,6-Di-tert-butyl-4-mercaptophenolHCID 2723922Sodium ethoxideHCID 5360545Sodium

Product 1

HCID 140118122,6-Bis(1,1-dimethylethyl)-4-[(2-hydroxy-1-methylpropyl)thio]phenol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
5 °C

Procedure

2,6-bis(1,1-Dimethylethyl)-4-mercaptophenol (18.2 g, 0.076 mole) was added to a solution of sodium ethoxide freshly prepared from sodium (3.5 g, 0.15 mole) in ethyl alcohol (100 ml) and stirred for 1 hour. After cooling to 5° C. with an ice bath, trans-2,3-epoxybutane (5.0 g, 0.069 mole) was added and the ice bath removed. After stirring for 5.5 hours the reaction mixture was poured into ten percent hydrochloric acid (50 ml). The ethyl alcohol was removed using a rotary evaporator and the aqueous residue extracted with ethyl acetate (2×75 ml). The extracts were combined, dried over sodium sulfate, filtered, and concentrated to an orange oil. The product was purified by chromatography on silica to give a yellow solid which was recrystallized from hexane to give a white solid, m.p. ca. 73° C.

Workup

  1. customthe ice bath removed
  2. stirringAfter stirring for 5.5 hours the reaction mixture
  3. additionwas poured into ten percent hydrochloric acid (50 ml)
  4. customThe ethyl alcohol was removed
  5. customa rotary evaporator
  6. extractionthe aqueous residue extracted with ethyl acetate (2×75 ml)
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated to an orange oil
  10. customThe product was purified by chromatography on silica
  11. customto give a yellow solid which
  12. customwas recrystallized from hexane
  13. customto give a white solid, m.p. ca. 73° C.

Sources & evidence

ORD record
ord-8feea872517749a49a131a8a4ed733b2
Source dataset
uspto-grants-1988_07
Patent number
US04755524

Reaction notes

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