P-Xylene → HCID 11557724, compound

HRID 1728991Notes

Reaction equation

F.[CH3:2][C:3]1[CH:4]=[CH:5][C:6]([CH3:9])=[CH:7][CH:8]=1.[C:10](OC)(=[O:19])/[CH:11]=[CH:12]/[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[CH3:2][C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[C:5]2[C:4]=1[CH:12]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:11][C:10]2=[O:19]

Participants

Reactant 3

HCID 7809P-Xylene

HCID 14917Hydrofluoric Acid

HCID 637520Methyl Cinnamate

Product 1

HCID 11557724HCID 11557724, compoundYield 90%

Conditions

Temperature: 70 °C

Procedure

100 g (5 mol) of anhydrous hydrogen fluoride were added to 10.6 g (100 mmol) of p-xylene (99% purity) and 17 g (105 mmol) of methyl trans-cinnamate, and the mixture was stirred at 70° C. for 17 hours. Work-up carried out analogously to Example A gave 23.6 g of a yellowish solid. The purity of the product is 96% (GC). (96% of theory). After recrystallization once from an ethyl acetate/hexane mixture (1:1), a virtually white solid was obtained in a yield of 90%. The purity after this step is greater than 98% (GC).

Workup

customAfter recrystallization once from an ethyl acetate/hexane mixture (1:1)
customa virtually white solid was obtained in a yield of 90%

Sources & evidence

ORD record: ord-67e2bb9da9cb40f5adc66ecba7d7e58f
Source dataset: uspto-grants-1994_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05329049

Reaction notes

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