Pinacol → iso-Propyl pinacol borate

HRID 473339Notes

Reaction equation

HRID 473339 reaction equation
[B:1]([O:10]C(C)C)([O:6]C(C)C)[O:2][CH:3]([CH3:5])[CH3:4].[OH:14][C:15]([C:18]([OH:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16]>>[B:1]([OH:10])([OH:6])[OH:2].[CH:3]([CH2:16][C:15]([C:18]([OH:21])([CH3:20])[CH3:19])([CH3:17])[OH:14])([CH3:5])[CH3:4]

Participants

3

Reactant 2

HCID 6425Pinacol2×HCID 21531Triisopropyl borate

Product 1

HCID 131731157iso-Propyl pinacol borate

Conditions

Temperature
90 °C

Procedure

To a 20 L four-neck bottle tri-isopropyl borate (261.0 g, 1.388 mol) and pinacol (142.5 g, 1.207 mol) were added and heated to ˜90° C. for 12-16 h. The criteria for a reaction completion is pinacol<4.0% by GC. After completion, the reaction was converted to distillation, and the product fractions (boiling at 174-178° C.) collected. Thus the title product was obtained as a colourless oil in a yield range of 80-90% th across the six 20 L batches which were operated. GC records purity of 87-96%, but 1H NMR shows the product to be very pure. [discrepancy due to product instability to GC conditions.]

Workup

  1. distillationAfter completion, the reaction was converted to distillation
  2. customthe product fractions (boiling at 174-178° C.) collected

Sources & evidence

ORD record
ord-c7d43591355445fcb2303cc2626195c8
Source dataset
uspto-grants-2014_01
Patent number
US08633319B2

Reaction notes

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