Tributyl borate → Dibutyl 2,6-di-tert-butyl-4-tolyl orthoborate

HRID 2164709Notes

Reaction equation

HRID 2164709 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:6]=1[OH:16])([CH3:4])([CH3:3])[CH3:2].[B:17](OCCCC)([O:23][CH2:24][CH2:25][CH2:26][CH3:27])[O:18][CH2:19][CH2:20][CH2:21][CH3:22]>>[B:17]([O:23][CH2:24][CH2:25][CH2:26][CH3:27])([O:18][CH2:19][CH2:20][CH2:21][CH3:22])[O:16][C:6]1[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:10][C:9]([CH3:11])=[CH:8][C:7]=1[C:12]([CH3:15])([CH3:14])[CH3:13]

Participants

3

Reactant 2

HCID 12712Tributyl borateHCID 314042,6-Di-tert-butyl-4-methylphenol

Product 1

HCID 76232Dibutyl 2,6-di-tert-butyl-4-tolyl orthoborate

Procedure

In a moisture-protected atmosphere, 2,6-di-tert-butyl-4-methylphenol (1543 g) was heated to 245° C. and while stirring tributyl borate (805.5 g) was slowly added drop by drop. The addition rate was controlled to maintain the reaction temperature at 230°-250° C. and butanol was distilled from the mixture as formed. The distillate was fractionated to separate butanol from tributyl borate and the latter was recycled to the reacting mixture. The reaction mixture was heated at 250°-260° C. until no further distillation was observed.

Workup

  1. temperatureto maintain the reaction temperature at 230°-250° C.
  2. distillationbutanol was distilled from the mixture
  3. customas formed
  4. customto separate butanol from tributyl borate
  5. temperatureThe reaction mixture was heated at 250°-260° C. until no further distillation

Sources & evidence

ORD record
ord-282a9e8886a349f2a29a8d0d69d5d932
Source dataset
uspto-grants-1985_03
Patent number
US04507216

Reaction notes

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