O-Cresol → HCID 57709044, compound

HRID 547135Notes

Reaction equation

FC(F)(F)C(O)=O.[CH2:8]([C:10]([C:14]1[CH:19]=[CH:18][C:17]([O:20][S:21]([C:24]([F:27])([F:26])[F:25])(=[O:23])=[O:22])=[C:16]([O:28][CH3:29])[CH:15]=1)(O)[CH2:11][CH3:12])[CH3:9].[C:30]1([CH3:37])[C:35]([OH:36])=[CH:34][CH:33]=[CH:32][CH:31]=1>>[CH2:8]([C:10]([C:14]1[CH:19]=[CH:18][C:17]([O:20][S:21]([C:24]([F:27])([F:26])[F:25])(=[O:23])=[O:22])=[C:16]([O:28][CH3:29])[CH:15]=1)([C:32]1[CH:33]=[CH:34][C:35]([OH:36])=[C:30]([CH3:37])[CH:31]=1)[CH2:11][CH3:12])[CH3:9]

Participants

Reactant 3

HCID 335O-Cresol

HCID 6422Trifluoroacetic acid

HCID 57454150HCID 57454150, compound

Product 1

HCID 57709044HCID 57709044, compoundYield 95%

Procedure

Trifluoromethanesulfonic anhydride (0.8 mL, 4.76 mmol) was added to a solution of 4-(1-ethyl-1-hydroxy-propyl)-2-methoxy-phenol (Example 176-(3); 1.0 g, 4.76 mmol) in pyridine (4 mL) at room temperature, and the mixture was stirred at room temperature for one hour. The reaction solution was extracted with ethyl acetate. The organic layer was washed with 1 N hydrochloric acid aqueous solution and brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (hexane only to hexane:ethyl acetate=1:1) to give trifluoromethanesulfonic acid 4-(1-ethyl-1-hydroxy-propyl)-2-methoxy-phenyl ester (1.51 g, 93%). Trifluoroacetic acid (0.1 mL) was added to a mixture of trifluoromethanesulfonic acid 4-(1-ethyl-1-hydroxy-propyl)-2-methoxy-phenyl ester (100 mg, 0.292 mmol) with o-cresol (68.2 mg, 585 mmol) at room temperature, and the mixture was stirred at room temperature for 16 hours. The mixture was concentrated under reduced pressure. Then, the resulting residue was purified by silica gel chromatography (hexane only to hexane:ethyl acetate=4:1) to give the title compound (0.12 g, 95%).

Workup

concentrationThe mixture was concentrated under reduced pressure
customThen, the resulting residue was purified by silica gel chromatography (hexane only to hexane

Sources & evidence

ORD record: ord-fb1c9181c7764039806761d7e759408a
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07935688B2

Reaction notes

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