Toluene → HCID 178419783, compound

HRID 1387198Notes

Reaction equation

HRID 1387198 reaction equation
[BH:1]([O:3][BH:4][OH:5])[OH:2].[C:6]1([CH3:12])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>>[CH:6]12[CH2:12][CH:6]3[CH2:11][CH:10]([CH2:9][CH:8]([CH2:7]3)[CH2:7]1)[CH2:11]2.[BH:1]1[O:3][BH:4][O:5][CH:12]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:9]([CH3:10])([CH3:8])[CH:12]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[O:2]1

Participants

3

Reactant 2

HCID 1140Toluene2×HCID 16070028HCID 16070028, compound

Product 1

HCID 178419783HCID 178419783, compound

Procedure

The above crude diboronic acid and 2,2-dimcthylporpane-1,3-diol (neopentyl glycol) (10.4 g, 0.1 mol) were dissolved in 300 mL of toluene and heated under vigorous reflux with a Dean-Stark trap overnight. After the completion of the reaction, toluene was evaporated and the crude product was recrystallized from toluene to give 7.10 g of product as white solid. 1H NMR (CDCl3) δ (ppm): 1.00 (s, 12H, CH3), 1.78 (s, 2H), 1.96 (s, 8H), 2.05 (s,2H) 2.30 (s, 2H), 3.74 (s, 4H, CH2), 7.37 (d, J=8.1 Hz, 4H, aromatic), 7.75 (d, J=8.1 Hz, 4H, aromatic); 13C NMR (CDCl3): 21.91, 29.60, 31.87, 35.97, 37.46, 42.23, 48.59, 72.28, 124.17, 128.16, 133.87, 153.21. M.p. 249-251° C.; FD-MS: m/z 512 (M+).

Workup

  1. temperatureheated
  2. temperatureunder vigorous reflux with a Dean-Stark trap overnight
  3. customwas evaporated
  4. customthe crude product was recrystallized from toluene

Sources & evidence

ORD record
ord-73680fbdbaeb4134ac2f2e46c3c27535
Source dataset
uspto-grants-2001_07
Patent number
US06268072B1

Reaction notes

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