Water → Benzyl 2-(4-oxocyclohexyl)acetate

HRID 1774388Notes

Reaction equation

HRID 1774388 reaction equation
C1O[C:4]2([CH2:9][CH2:8][CH:7]([CH2:10][C:11]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[O:12])[CH2:6][CH2:5]2)[O:3]C1.O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>CC(C)=O.CCCCCC.C(OCC)(=O)C>[O:3]=[C:4]1[CH2:9][CH2:8][CH:7]([CH2:10][C:11]([O:13][CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[O:12])[CH2:6][CH2:5]1

Participants

7

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 590090264-Benzyloxycarbonylmethylcyclohexanone ethylene acetal

Product 1

HCID 58069819Benzyl 2-(4-oxocyclohexyl)acetateYield 86.3%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of 4-benzyloxycarbonylmethylcyclohexanone ethylene acetal (7.62 g, 26.2 mmol) in acetone (235 mL)-water (10 mL) was added p-toluenesulfonic acid monohydrate (221 mg, 1.16 mmol), and the mixture was stirred at 55° C. for 10 h. The reaction mixture was adjusted to pH 5 with sodium hydrogen carbonate with stirring under ice cooling, and concentrated under reduced pressure. The residue obtained by azeotropic distillation with the addition of toluene was subjected to silica gel column chromatography (hexane-ethyl acetate 4:1) to give 5.57 g of benzyl 2-(4-oxocyclohexyl)acetate as oil (yield: 86%).

Workup

  1. stirringwith stirring under ice cooling
  2. concentrationconcentrated under reduced pressure
  3. customThe residue obtained by azeotropic distillation with the addition of toluene

Sources & evidence

ORD record
ord-ad1340270df64e23afe05ebdd5d6c37d
Source dataset
uspto-grants-2016_02
Patent number
US09260375B2

Reaction notes

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