Boron trifluoride → HCID 23454582, compound

HRID 1680806Notes

Reaction equation

HRID 1680806 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([OH:13])=O)=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:14]([OH:16])=O.[CH3:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[C:19]=1[OH:25].F.B(F)(F)F.[C:31](=[O:34])(O)[O-].[Na+]>O>[CH3:4][C:3]1[CH:2]=[C:1]([CH:10]=[C:9]([CH3:8])[C:31]=1[OH:34])[C:11]([C:7]1[CH:8]=[CH:9][C:10]2[C:5](=[CH:4][CH:3]=[C:2]([C:14](=[O:16])[C:22]3[CH:21]=[C:20]([CH3:24])[C:19]([OH:25])=[C:18]([CH3:17])[CH:23]=3)[CH:1]=2)[CH:6]=1)=[O:13]

Participants

7

Reactant 5

HCID 6356Boron trifluorideHCID 113352,6-DimethylphenolHCID 143572,6-Naphthalenedicarboxylic acidHCID 14917Hydrofluoric AcidHCID 516892Sodium Bicarbonate

Product 1

HCID 23454582HCID 23454582, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

2,6-Naphthalenedicarboxylic acid (108 g, 0.50 mole) and 2,6-dimethylphenol (122 g, 1.00 mole) were charged to a one-liter Hastalloy C® shaker tube. The tube was cooled and charged with hydrogen fluoride (400 g) and boron trifluoride (150 g). It was then heated to 50° C. and shaken for 4 hr at 50° C. The tube was cooled and vented, and the contents, a red solid in a red solution, was allowed to evaporate in the hood. The resulting red solid was stirred in 2 l. of water, warmed, and isolated by filtration of the warm solution. The precipitate was stirred with 2 l. of water, warmed, and neutralized with sodium bicarbonate. The warm mixture was filtered and the precipitate was washed with water, then methanol, and air dried. There was obtained 192.5 g (91%) of crude 2,6-bis(3,5-dimethyl-4-hydroxybenzoyl)naphthalene as an orange powder. 2,6-Bis(4-acetoxy-3,5-dimethylbenzoyl)naphthalene, the diacetate of the above diol was prepared in a manner generally similar to that of Example 2. It had a m.p. (differential scanning calorimetry) of 302° C., and its elemental analysis is consistent with the formula C32H28O6.

Workup

  1. temperatureThe tube was cooled
  2. temperatureThe tube was cooled
  3. customto evaporate in the hood
  4. stirringThe resulting red solid was stirred in 2 l
  5. temperatureof water, warmed
  6. customisolated by filtration of the warm solution
  7. stirringThe precipitate was stirred with 2 l
  8. filtrationThe warm mixture was filtered
  9. washthe precipitate was washed with water
  10. dry with materialmethanol, and air dried

Sources & evidence

ORD record
ord-0e76d7825e8246ab8c64a93b93c1d6c3
Source dataset
uspto-grants-1981_06
Patent number
US04276226

Reaction notes

Loading…