Boron trifluoride → HCID 20213781, compound

HRID 903307Notes

Reaction equation

HRID 903307 reaction equation
ClCl.[H][H].F.B(F)(F)F.[C:10]([OH:21])(=O)[C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=O)=[CH:13][CH:12]=1.[CH3:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[C:24]=1[OH:30]>>[CH3:22][C:23]1[CH:28]=[C:27]([CH:26]=[C:25]([CH3:29])[C:24]=1[OH:30])[C:15]([C:14]1[CH:13]=[CH:12][C:11]([C:10](=[O:21])[C:27]2[CH:26]=[C:25]([CH3:29])[C:24]([OH:30])=[C:23]([CH3:22])[CH:28]=2)=[CH:19][CH:18]=1)=[O:17]

Participants

7

Reactant 6

HCID 6356Boron trifluoride2×HCID 7489Terephthalic AcidHCID 113352,6-DimethylphenolHCID 14917Hydrofluoric Acid2×HCID 24526ChlorineHCID 178418361HCID 178418361, compound

Product 1

HCID 20213781HCID 20213781, compoundYield 79%

Conditions

Temperature
50 °C

Procedure

The diketodiols and diketodiesters of the formula ##STR8## where X is methyl or chlorine, Ar is m- or p-phenylene and R is hydrogen or hydrocarbyl of from 1-10 carbon atoms are prepared by reacting, under anhydrous conditions, a disubstituted monophenol, such as 2,6-dimethyl- or 2,6-dichlorophenol with terephthalic (for Ar=p-phenylene) or isophthalic (for Ar=m-phenylene) acid (or its diester) or hydrogen fluoride in the presence of boron trifluoride. The reaction is allowed to proceed to about 0° to about 100° C. For example, terephthalic acid (83 g) and 2,6-dimethylphenol (122 g) are charged to a 1 liter Hastalloy C® shaker tube. The tube was cooled and then charged with hydrogen fluoride (400 g) and boron trifluoride (150 g). It was warmed to 50° C., shaken at 50° C. for 4 hr, then cooled and vented. The contents, a dark red solid in a dark red solution, were allowed to evaporate in the hood to afford crude 1,4-bis(3,5-dimethyl-4-hydroxybenzoyl)benzene as a dark red solid. This material was stirred with 2 l. of water, warmed and isolated by filtration of the warm mixture. It was again stirred with 2 l. of water, warmed, neutralized with sodium bicarbonate, and isolated by filtration of the warm mixture. After being washed with water and air dried, the product was obtained as a tan powder in a yield of 79%.

Workup

  1. customare prepared
  2. customto proceed to about 0° to about 100° C
  3. temperatureThe tube was cooled
  4. temperaturecooled
  5. customto evaporate in the hood

Sources & evidence

ORD record
ord-7023b1b644894b06bf94c1b88db1f3e2
Source dataset
uspto-grants-1980_10
Patent number
US04226970

Reaction notes

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