Acetic Anhydride → trans-Racemic-2-phenylcyclohexyl acetate

HRID 929180

Reaction equation

HRID 929180 reaction equation
[C:1]1([C@@H:7]2[CH2:12][CH2:11][CH2:10][CH2:9][C@H:8]2[OH:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.FC(F)(F)S([O-])(=O)=O.[Sn+2].FC(F)(F)S([O-])(=O)=O.[C:31](OC(=O)C)(=[O:33])[CH3:32].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[C:31]([O:13][C@@H:8]1[CH2:9][CH2:10][CH2:11][CH2:12][C@H:7]1[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)(=[O:33])[CH3:32]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 102793rel-(1R,2S)-2-PhenylcyclohexanolHCID 516892Sodium BicarbonateHCID 2776843Tin(II) trifluoromethanesulfonate

Product 1

HCID 11009435trans-Racemic-2-phenylcyclohexyl acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of trans-racemic-2-phenylcyclohexanol (4.63 g, 26.3 mmol) and tin(II)trifluoromethanesulfonate (219 mg, 0.525 mmol) under nitrogen in anhydrous DCM (100 ml) at room temperature was added acetic anhydride (3.72 ml, 4.02 g, 39.4 mmol) in one portion. The mixture was stirred for 18 hours at room temperature. The mixture was poured into saturated aqueous sodium bicarbonate (200 ml). The mixture was extracted with DCM (2×200 ml). The combined organic layers were washed with brine (70 ml), dried over sodium sulfate, and concentrated under reduced pressure to provide the desired product as a light yellow oil. LC-MS: calculated for C14H18O2 218.29 observed m/e: 219.33 (M+H)+ (Rt 0.93/2 min)

Workup

  1. extractionThe mixture was extracted with DCM (2×200 ml)
  2. washThe combined organic layers were washed with brine (70 ml)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-61acf6a0ada5406db8c9393079df05f7
Source dataset
uspto-grants-2016_03
Patent number
US09290517B2

Linked notes

Loading…