2,6-Di-tert-butyl-4-mercaptophenol → HCID 14011801, compound

HRID 845078Notes

Reaction equation

HRID 845078 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-:17][CH2:18][CH3:19].[Na+].[Na].C[O:23][C:24](=O)[CH2:25][S:26]([CH2:28][CH2:29]Cl)=[O:27]>C(O)C.O>[CH2:18]([O:17][C:24](=[O:23])[CH2:25][S:26]([CH2:28][CH2:29][S:11][C:9]1[CH:8]=[C:7]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:6]([OH:16])=[C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[CH:10]=1)=[O:27])[CH3:19]

Participants

7

Reactant 4

HCID 703702,6-Di-tert-butyl-4-mercaptophenolHCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 20133529HCID 20133529, compound

Product 1

HCID 14011801HCID 14011801, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

2,6-bis(1,1-Dimethylethyl)-4-mercaptophenol (2.97 g, 0.0125 mole) was added to sodium ethoxide, freshly prepared from sodium (0.29 g, 0.0125 mole) in ethyl alcohol (75 ml), and stirred for 1.5 hours. A solution of the title compound of Example 11 (2.3 g, 0.0125 mole) in ethyl alcohol (50 ml) was added dropwise over one hour and the resulting solution stirred for 20 hours at room temperature. Water (100 ml) was added and the ethyl alcohol removed using a rotary evaporator. The aqueous residue was extracted with ethyl acetate (2×100 ml). The combined organic extracts were dried over sodium sulfate, filtered, concentrated and the product purified by chromatography on silica. The yellow solid was recrystallized from ethyl acetate/hexane to give 1.1 g, m.p. ca. 110° C.

Workup

  1. stirringthe resulting solution stirred for 20 hours at room temperature
  2. customthe ethyl alcohol removed
  3. customa rotary evaporator
  4. extractionThe aqueous residue was extracted with ethyl acetate (2×100 ml)
  5. dry with materialThe combined organic extracts were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customthe product purified by chromatography on silica
  9. customThe yellow solid was recrystallized from ethyl acetate/hexane
  10. customto give 1.1 g, m.p. ca. 110° C.

Sources & evidence

ORD record
ord-1443b8d4b935406e81ed8ecce3f69672
Source dataset
uspto-grants-1988_07
Patent number
US04755524

Reaction notes

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