Water → HCID 13390906, compound

HRID 1980804Notes

Reaction equation

HRID 1980804 reaction equation
[B:1]([OH:4])([OH:3])[OH:2].[CH2:5]([NH2:17])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[CH3:18][C:19]1[CH:27]=[CH:26][C:22]([CH:23]2O[CH2:24]2)=[CH:21][CH:20]=1.O>C1(C)C=CC=CC=1>[OH:2][B:1]1[O:4][CH2:24][CH:23]([C:22]2[CH:26]=[CH:27][C:19]([CH3:18])=[CH:20][CH:21]=2)[N:17]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH:23]([C:22]2[CH:26]=[CH:27][C:19]([CH3:18])=[CH:20][CH:21]=2)[CH2:24][O:3]1

Participants

6

Reactant 4

HCID 962Water3×HCID 7628Boric Acid3×HCID 13583DodecylamineHCID 1081112-(4-Methylphenyl)oxirane

Product 1

HCID 13390906HCID 13390906, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Procedure

The boramid compound, 1-hydroxy-4,6-dicresyl-5-dodecyl-5-aza-1-bora-2,8-dioxacyclooctane is prepared by adding 21 grams of boric acid with 61.7 grams of dodecylamine, 89.3 grams of para methylstyrene oxide and 250 ml of toluene to a single necked one liter round-bottomed flask. The toluene acts as a solvent and as an azeotrope for water produced during the reaction. It should be noted that boric acid is not soluble in toluene. The flask is placed in a heating mantle and fitted with a Dean Stark trap that is topped with a water-cooled condenser. The mixture thus formed is heated until it begins to reflux. Next, the mantle heat is adjusted to give a moderate reflux rate. The reaction mixture is refluxed for one hour, or until the stoichiometric amount of water (12 ml) collects in the Dean-Stark trap and all of the boric acid has dissolved, after which the toluene is distilled from the reaction product. The reaction produces 160 grams of product.

Workup

  1. customproduced during the reaction
  2. customfitted with a Dean Stark trap that
  3. temperaturecooled condenser
  4. customThe mixture thus formed
  5. temperatureis heated until it
  6. temperatureto reflux
  7. temperatureNext, the mantle heat
  8. customto give a moderate reflux rate
  9. temperatureThe reaction mixture is refluxed for one hour
  10. distillationafter which the toluene is distilled from the reaction product

Sources & evidence

ORD record
ord-1d0c4deac1ae4e94a0aab5d681efad58
Source dataset
uspto-grants-1985_04
Patent number
US04511516

Reaction notes

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