Styrene Oxide → HCID 13751861, compound

HRID 845189Notes

Reaction equation

HRID 845189 reaction equation
[CH2:1]([NH2:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[CH2:20]1[O:28][CH:21]1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[B:29]([OH:32])(O)[OH:30]>O>[B:29].[OH:30][B:29]1[O:28][CH:21]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:20][N:19]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:20][CH:21]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[O:32]1

Participants

6

Reactant 3

HCID 7276Styrene OxideHCID 7628Boric AcidHCID 15793Octadecylamine

Product 2

HCID 5462311BoronHCID 13751861HCID 13751861, compoundYield 195.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent4×

Procedure

A boron compound of the invention is prepared by adding 17,093 grams of octadecylamine and 15,362 grams of styrene oxide to a 65-liter, round-bottomed flask that contains 13 liters of tollene and 1 liter of water. The flask is fitted with a water-cooled condenser and placed in a heating mantle. The mixture thus formed is refluxed at a moderate rate for 24 hours. The reaction is cooled to room temperature and 4,033 grams of boric acid are added to the flask. Next, the flask is fitted with a Dean-Stark trap, topped with a water-cooled condenser and the reaction mixture is refluxed until water stops collecting in the trap. Toluene is distilled from the reaction product to an end-point temperature of 400° F. The reaction produces 34,183 grams of 1-hydroxy-3,7-diphenyl-5-octadecyl-5-aza-1-bora-2,8-dioxacyclooctane.

Workup

  1. temperaturecooled condenser
  2. customThe mixture thus formed
  3. temperatureis refluxed at a moderate rate for 24 hours
  4. customNext, the flask is fitted with a Dean-Stark trap
  5. temperaturecooled condenser
  6. customstops collecting in the trap
  7. distillationToluene is distilled from the reaction product to an end-point temperature of 400° F

Sources & evidence

ORD record
ord-7b49c055a97e4b21af1f98963307d906
Source dataset
uspto-grants-1988_07
Patent number
US04756842

Reaction notes

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