Water → HCID 13390906, compound

HRID 1154504Notes

Reaction equation

HRID 1154504 reaction equation
[CH2:1]([NH2:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[CH3:14][C:15]1[CH:23]=[CH:22][C:18]([CH:19]2[O:21][CH2:20]2)=[CH:17][CH:16]=1.O.[B:25]([OH:28])(O)[OH:26]>C1(C)C=CC=CC=1>[OH:26][B:25]1[O:21][CH2:20][CH:19]([C:18]2[CH:22]=[CH:23][C:15]([CH3:14])=[CH:16][CH:17]=2)[N:13]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH:19]([C:18]2[CH:22]=[CH:23][C:15]([CH3:14])=[CH:16][CH:17]=2)[CH2:20][O:28]1

Participants

6

Reactant 4

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

Product 1

HCID 13390906HCID 13390906, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

The boramid compound, 1-hydroxy-4,6-dicresyl-5-dodecyl-5-aza-1-bora-2,8-dioxacyclooctane is prepared by adding 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. 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 24 hours. The reaction mixture is cooled to room temperature and 21 grams of boric acid are added to the flask. Next, the flask is equipped with a Dean-Stark trap topped with a water-cooled condenser and the reaction mixture is refluxed until water stops collecting in the trap (12 ml). Toluene is distilled from the reaction product. The reaction produces 160 grams of product.

Workup

  1. customproduced during the reaction
  2. customThe mixture thus formed
  3. temperatureis heated until it
  4. temperatureto reflux
  5. temperatureNext, the mantle heat
  6. customto give a moderate reflux rate
  7. temperatureThe reaction mixture is refluxed for 24 hours
  8. customNext, the flask is equipped with a Dean-Stark trap
  9. temperaturecooled condenser
  10. customstops collecting in the trap (12 ml)
  11. distillationToluene is distilled from the reaction product

Sources & evidence

ORD record
ord-7426c915daf7452e81dc3a4ad4dcd65d
Source dataset
uspto-grants-1984_12
Patent number
US04490265

Reaction notes

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