Boron trifluoride → 4-Methyl-2,2,4-tris(3,5-di-tert-butyl-4-hydroxyphenylthio)pentane

HRID 65168Notes

Reaction equation

HRID 65168 reaction equation
B(F)(F)F.[CH3:5][C:6]([S:12][C:13]1[CH:18]=[C:17]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:16]([OH:23])=[C:15]([C:24]([CH3:27])([CH3:26])[CH3:25])[CH:14]=1)([CH3:11])[CH2:7]C(=O)C.[C:28]([C:32]1[CH:37]=[C:36]([SH:38])[CH:35]=[C:34]([C:39]([CH3:42])([CH3:41])[CH3:40])[C:33]=1[OH:43])([CH3:31])([CH3:30])[CH3:29]>C1(C)C=CC=CC=1>[CH3:5][C:6]([S:12][C:13]1[CH:14]=[C:15]([C:24]([CH3:27])([CH3:25])[CH3:26])[C:16]([OH:23])=[C:17]([C:19]([CH3:22])([CH3:20])[CH3:21])[CH:18]=1)([CH3:11])[CH2:7][C:6]([S:12][C:13]1[CH:18]=[C:17]([C:19]([CH3:21])([CH3:20])[CH3:22])[C:16]([OH:23])=[C:15]([C:24]([CH3:25])([CH3:27])[CH3:26])[CH:14]=1)([S:38][C:36]1[CH:35]=[C:34]([C:39]([CH3:42])([CH3:41])[CH3:40])[C:33]([OH:43])=[C:32]([C:28]([CH3:31])([CH3:30])[CH3:29])[CH:37]=1)[CH3:5]

Participants

5

Reactant 3

HCID 6356Boron trifluorideHCID 703702,6-Di-tert-butyl-4-mercaptophenolHCID 136435724-Methyl-4-(3,5-di-tert-butyl-4-hydroxyphenylthio)-2-pentanone

Product 1

HCID 136435734-Methyl-2,2,4-tris(3,5-di-tert-butyl-4-hydroxyphenylthio)pentane

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

0.11 Grams of BF3 -etherate is added to a solution of 2.70 grams of the product from (a) and 4.14 grams of 2,6-di-tert-butyl-4-mercaptophenol dissolved in 30 ml of toluene. The mixture is heated at 55°-65° C. for nine hours and 105°-110° C. for three additional hours. The toluene solution is washed with water and dried over sodium sulfate. The residue, isolated by evaporation of the solvent by distillation in vacuum, is purified by passing a solution in 70:30 heptane:toluene through a flash chromatographic column using silica gel. The isolated residue solidifies on cooling, and melts at 93°-115° C.

Workup

  1. temperatureThe mixture is heated at 55°-65° C. for nine hours and 105°-110° C. for three additional hours
  2. washThe toluene solution is washed with water
  3. dry with materialdried over sodium sulfate
  4. customThe residue, isolated by evaporation of the solvent by distillation in vacuum
  5. customis purified
  6. temperatureon cooling

Sources & evidence

ORD record
ord-4c23619940e94a48b5a59a1bd80b3420
Source dataset
uspto-grants-1986_09
Patent number
US04612341

Reaction notes

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