Hydrochloric Acid → 4-(2-Benzyloxyethyl)cyclohexanone

HRID 1518083Notes

Reaction equation

HRID 1518083 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH:11]1[CH2:20][CH2:19][C:14]2(OCC[O:15]2)[CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C([O-])(O)=O.[Na+]>C1COCC1>[CH2:1]([O:8][CH2:9][CH2:10][CH:11]1[CH2:12][CH2:13][C:14](=[O:15])[CH2:19][CH2:20]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 218796038-[2-(Benzyloxy)ethyl]-1,4-dioxaspiro[4.5]decane

Product 1

HCID 218796054-(2-Benzyloxyethyl)cyclohexanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of crude 8-[2-(benzyloxy)ethyl]-1,4-dioxaspiro[4.5]decane (227.8 g) in THF (500 mL) is added 5N HCl (600 mL) at room temperature, and the mixture is stirred for 10 hours at the same temperature. After addition of NaHCO3 aq. (300 g in 500 mL water), the mixture is extracted with EtOAc (1500 mL). The water layer is extracted with EtOAc (1000 mL×2), and the combined organic layer is washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. The crude mixture is purified by silica gel column chromatography to afford 4-(2-benzyloxyethyl)cyclohexanone.

Workup

  1. extractionthe mixture is extracted with EtOAc (1500 mL)
  2. extractionThe water layer is extracted with EtOAc (1000 mL×2)
  3. washthe combined organic layer is washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe crude mixture is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ec2494eca42e4d4a8cf0382392fab16e
Source dataset
uspto-grants-2012_07
Patent number
US08232403B2

Reaction notes

Loading…