Water → Cyclohexaneacetic acid, 4-[4-[[(trifluoroMethyl)sulfonyl]oxy]phenyl]-, Methyl ester, trans-

HRID 632931Notes

Reaction equation

HRID 632931 reaction equation
C(N(CC)CC)C.[CH3:8][O:9][C:10](=[O:25])[CH2:11][CH:12]1[CH2:17][CH2:16][CH:15]([C:18]2[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=2)[CH2:14][CH2:13]1.[F:26][C:27]([F:33])([F:32])[S:28](O)(=[O:30])=[O:29].O>C(Cl)Cl>[CH3:8][O:9][C:10](=[O:25])[CH2:11][CH:12]1[CH2:13][CH2:14][CH:15]([C:18]2[CH:19]=[CH:20][C:21]([O:24][S:28]([C:27]([F:33])([F:32])[F:26])(=[O:30])=[O:29])=[CH:22][CH:23]=2)[CH2:16][CH2:17]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 62406Trifluoromethanesulfonic acidHCID 56971748Methyl 2-((1s,4s)-4-(4-hydroxyphenyl)cyclohexyl)acetate

Product 1

HCID 58909683Cyclohexaneacetic acid, 4-[4-[[(trifluoroMethyl)sulfonyl]oxy]phenyl]-, Methyl ester, trans-Yield 91.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethyl amine (8.1 mL, 57.99 mmol) was added dropwise to [4-(4-hydroxyphenyl)cyclohexyl]acetic acid methyl ester (9.6 g, 38.66 mmol) dissolved in CH2Cl2 and trifluoromethane sulphonic acid (8.1 mL, 48.32 mmol) solution at 0° C. The reaction mixture was warmed up to reach ambient temperature and stirred for 5 hours. The reaction mixture was poured into 200 mL water and extracted with CH2Cl2. The organic phase was washed with saturated sodium bicarbonate solution, brine and anhydrous Na2SO4. The solvent was reduced under reduced pressure, the residue was purified in silica gel using CH2Cl2 as an eluent to obtain [4-(4-trifluoromethanesulfonyloxyphenyl)cyclohexyl]acetic acid methyl ester (13.4 g, 91%) as a white solid.

Workup

  1. customat 0° C
  2. temperatureThe reaction mixture was warmed up
  3. customto reach ambient temperature
  4. extractionextracted with CH2Cl2
  5. washThe organic phase was washed with saturated sodium bicarbonate solution, brine and anhydrous Na2SO4
  6. customthe residue was purified in silica gel

Sources & evidence

ORD record
ord-d85bae9eaf224c7da63663a9bcb4f1f1
Source dataset
uspto-grants-2016_04
Patent number
US09321728B2

Reaction notes

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