Tributyl borate → HCID 20495657, compound

HRID 1074525Notes

Reaction equation

[B:1](OCCCC)(OCCCC)[O:2][CH2:3][CH2:4][CH2:5][CH3:6].[C:17]([C:21]1[CH:26]=[C:25]([CH3:27])[CH:24]=[C:23]([C:28]([CH3:31])([CH3:30])[CH3:29])[C:22]=1[OH:32])([CH3:20])([CH3:19])[CH3:18].[CH3:33][CH:34]1[CH:39]([CH3:40])[CH2:38][CH2:37][CH:36]([OH:41])[CH2:35]1>C(O)CCC>[B:1]([O:32][C:22]1[C:21]([C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:26][C:25]([CH3:27])=[CH:24][C:23]=1[C:28]([CH3:31])([CH3:30])[CH3:29])([O:41][CH:36]1[CH2:37][CH2:38][CH:39]([CH3:40])[CH:34]([CH3:33])[CH2:35]1)[O:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

Conditions

Temperature: 280 °C

Procedure

n-butyl 3,4-dimethylcyclohexyl 2,6-di-t-butyl-4-methylphenyl borate was prepared by successively transesterifying tri-n-butyl borate with 2,6-di-t-butyl-4-methylphenol and 3,4-dimethylcyclohexanol. Tri-n-butyl borate (1 mole) and 2,6-di-t-butyl-4-methylphenol (1 mole) were heated, with stirring, to a temperature of 280° C. and n-butanol collected as a distillate. After seven hours 0.81 moles had been collected and a total of 0.82 moles collected after ten hours. After cooling the reaction vessel and adding 1 mole of 3,4-dimethylcyclohexanol, the reaction mixture was again heated to 280° C. for six hours, after which time a further 0.9 moles of n-butanol had been collected. Volatile components were then removed under reduced pressure (90° C./0.1 mm) to leave a viscous golden yellow liquid as product.

Workup

distillationcollected as a distillate
customAfter seven hours 0.81 moles had been collected
customa total of 0.82 moles collected after ten hours
temperatureAfter cooling the reaction vessel
customVolatile components were then removed under reduced pressure (90° C./0.1 mm)
customto leave a viscous golden yellow liquid as product

Sources & evidence

ORD record: ord-a032efb2f125400d83e74f09b083d0aa
Source dataset: uspto-grants-1983_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04392973

Reaction notes

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