1,2-Dichloroethane → Benzyl 3-oxocyclohexanecarboxylate

HRID 340771Notes

Reaction equation

HRID 340771 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][CH2:5][CH:4]([C:8]([OH:10])=[O:9])[CH2:3]1.C(Cl)CCl.[CH2:15](O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[O:1]=[C:2]1[CH2:7][CH2:6][CH2:5][CH:4]([C:8]([O:10][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:9])[CH2:3]1

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 244Benzyl AlcoholHCID 27602523-Oxocyclohexane-1-carboxylic acid

Product 1

HCID 58964377Benzyl 3-oxocyclohexanecarboxylate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-oxocyclohexane carboxylic acid (1.5 g, 10.6 mmol) in CH2Cl2 (35 mL) were added DMAP (0.129 g, 1.06 mmol), EDC (4.05 g, 21.1 mmol), and BnOH (1.2 mL, 11.6 mmol). The reaction was maintained at ambient temperature for 1 h. The reaction was further diluted with CH2Cl2, and then washed with saturated aqueous NaHCO3, followed by brine. The organic layer was separated, dried with MgSO4, filtered, and concentrated. The resulting crude product was used in the next step without further purification. LCMS: calculated for C14H16O3 232.28, observed m/e 233.1 (M+H)+ 255.0 (M+Na) (Rt 1.74/4 min).

Workup

  1. washwashed with saturated aqueous NaHCO3
  2. customThe organic layer was separated
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting crude product was used in the next step without further purification
  7. customm/e 233.1 (M+H)+ 255.0 (M+Na) (Rt 1.74/4 min)

Sources & evidence

ORD record
ord-600420e4e06b4ac9b8846904f3bc01a7
Source dataset
uspto-grants-2014_11
Patent number
US08895596B2

Reaction notes

Loading…