Triethylamine → 4-Methyl-4-(3,5-di-tert-butyl-4-hydroxyphenylthio)-2-pentanone

HRID 638462Notes

Reaction equation

HRID 638462 reaction equation
[O:1]=[C:2]([CH:4]=[C:5]([CH3:7])[CH3:6])[CH3:3].[C:8]([C:12]1[CH:17]=[C:16]([SH:18])[CH:15]=[C:14]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:13]=1[OH:23])([CH3:11])([CH3:10])[CH3:9].C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH3:6][C:5]([S:18][C:16]1[CH:15]=[C:14]([C:19]([CH3:20])([CH3:21])[CH3:22])[C:13]([OH:23])=[C:12]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:17]=1)([CH3:7])[CH2:4][C:2](=[O:1])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8858Mesityl oxideHCID 703702,6-Di-tert-butyl-4-mercaptophenol

Product 1

HCID 136435724-Methyl-4-(3,5-di-tert-butyl-4-hydroxyphenylthio)-2-pentanone

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

8.48 Grams of mesityl oxide (0.084 moles) is added dropwise to a solution of 21.0 grams of 2,6 di-tert-butyl-4-mercaptophenol (0.088 moles) and one gram of triethylamine in 30 ml of toluene. The mixture is heated at 50°-55° C. for six hours. The solvent is then stripped off under vacuum and the residue retained at 60°-65° C. and 0.20 mm. Hg. for two hours. The residue is dissolved in toluene and purified by flash chromatography using silica gel. The product is isolated from solution by distilling off the volatiles under vacuum to a final pressure of 0.10 mm. Hg for five hours.

Workup

  1. temperatureThe mixture is heated at 50°-55° C. for six hours
  2. customretained at 60°-65° C.
  3. custompurified by flash chromatography
  4. customThe product is isolated from solution
  5. distillationby distilling off the volatiles under vacuum to a final pressure of 0.10 mm. Hg for five hours

Sources & evidence

ORD record
ord-778390fe3ed948098b8baa579d63e561
Source dataset
uspto-grants-1985_12
Patent number
US04560799

Reaction notes

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