Pyridine → Trifluoromethanesulfonic acid 4-[1-ethyl-1-(4-hydroxy-3-methyl-phenyl)-propyl]-2-methyl-phenyl ester

HRID 546804Notes

Reaction equation

HRID 546804 reaction equation
N1C=CC=CC=1.[F:7][C:8]([F:21])([F:20])[S:9]([O:12]S(C(F)(F)F)(=O)=O)(=[O:11])=[O:10].[OH:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]([C:34]2[CH:39]=[CH:38][C:37](O)=[C:36]([CH3:41])[CH:35]=2)([CH2:32][CH3:33])[CH2:30][CH3:31])=[CH:25][C:24]=1[CH3:42].C(OCC)(=O)C>ClCCl>[CH2:30]([C:29]([C:34]1[CH:39]=[CH:38][C:37]([O:12][S:9]([C:8]([F:21])([F:20])[F:7])(=[O:11])=[O:10])=[C:36]([CH3:41])[CH:35]=1)([C:26]1[CH:27]=[CH:28][C:23]([OH:22])=[C:24]([CH3:42])[CH:25]=1)[CH2:32][CH3:33])[CH3:31]

Participants

6

Reactant 4

HCID 1049PyridineHCID 8857Ethyl AcetateHCID 67749Trifluoromethanesulfonic anhydrideHCID 155213933,3-Bis[4-hydroxy-3-methylphenyl]pentane

Product 1

HCID 58598300Trifluoromethanesulfonic acid 4-[1-ethyl-1-(4-hydroxy-3-methyl-phenyl)-propyl]-2-methyl-phenyl esterYield 37.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pyridine (3 mL, 37.2 mmol) and trifluoromethanesulfonic anhydride (5.7 mL, 34.7 mmol) were added to a solution of 3,3-bis[4-hydroxy-3-methylphenyl]pentane (9.0 g, 31.6 mmol) in dichloromethane (300 mL) at 0° C., and then the mixture was stirred at the same temperature for one hour. Ethyl acetate was added to the reaction mixture. The organic layer was washed with a saturated aqueous sodium bicarbonate solution and brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by a silica gel column (hexane/ethyl acetate=10/1 to ethyl acetate only) to give the title compound (4.9 g, 37%).

Workup

  1. washThe organic layer was washed with a saturated aqueous sodium bicarbonate solution and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by a silica gel column (hexane/ethyl acetate=10/1 to ethyl acetate only)

Sources & evidence

ORD record
ord-173e444049ab4709b30b9a234b10b347
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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