Hydrochloric Acid → 4-(2-Benzyloxyethyl)cyclohexanone

HRID 1960039Notes

Reaction equation

HRID 1960039 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-8f1352d65ea74d7fbb28e235a71c8e40
Source dataset
uspto-grants-2013_04
Patent number
US08410275B2

Reaction notes

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