Boron trifluoride → HCID 20510741, compound

HRID 1680805Notes

Reaction equation

HRID 1680805 reaction equation
[C:1]([OH:12])(=O)[C:2]1[CH:10]=[CH:9][CH:8]=[C:4]([C:5]([OH:7])=O)[CH:3]=1.[CH3:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[C:15]=1[OH:21].F.B(F)(F)F.[C:27](=[O:30])(O)[O-].[Na+]>O>[CH3:5][C:4]1[CH:3]=[C:2]([CH:10]=[C:9]([CH3:8])[C:27]=1[OH:30])[C:5]([C:4]1[CH:8]=[CH:9][CH:10]=[C:2]([C:1](=[O:12])[C:18]2[CH:17]=[C:16]([CH3:20])[C:15]([OH:21])=[C:14]([CH3:13])[CH:19]=2)[CH:3]=1)=[O:7]

Participants

7

Reactant 5

HCID 6356Boron trifluorideHCID 8496Isophthalic AcidHCID 113352,6-DimethylphenolHCID 14917Hydrofluoric AcidHCID 516892Sodium Bicarbonate

Product 1

HCID 20510741HCID 20510741, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Isophthalic acid (66 g, 0.40 mole) and 2,6-dimethylphenol (96 g, 0.80 mole) were charged to a one-liter Hastalloy C® shaker tube. The tube was cooled and hydrogen fluoride (400 g) was condensed in. The tube was then warmed to room temperature and pressured to 50 psig with boron trifluoride. The tube was then warmed to 50° C. and shaken 4 hr at 50° C. After being cooled and vented, the tube was discharged of its contents which was a dark red solution. This solution was allowed to evaporate in the hood. The dark red solid which resulted was stirred in 2 l. of water, heated to boiling, and the solid was isolated by filtration of the hot slurry. The precipitate was stirred in 2 l. of water, heated to boiling, and neutralized with sodium bicarbonate. Filtration of the hot slurry and air drying of the precipitate afforded the title product as a salmon-colored powder with an i.r. spectrum identical with that of the analytical sample. The yield was 136.5 g (91%).

Workup

  1. temperatureThe tube was cooled
  2. customcondensed in
  3. temperatureThe tube was then warmed to 50° C.
  4. temperatureAfter being cooled
  5. customto evaporate in the hood
  6. customThe dark red solid which resulted
  7. stirringwas stirred in 2 l
  8. customthe solid was isolated by filtration of the hot slurry
  9. stirringThe precipitate was stirred in 2 l
  10. filtrationFiltration of the hot slurry and air
  11. customdrying of the precipitate

Sources & evidence

ORD record
ord-9b7b3acbc06a4fff8831715f02c6a4f2
Source dataset
uspto-grants-1981_06
Patent number
US04276226

Reaction notes

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