Hydrochloric Acid → Cyclohexanone, 4-[(phenylmethoxy)methyl]-

HRID 1960027Notes

Reaction equation

HRID 1960027 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]1[CH2:19][CH2:18][C:13]2(OCC[O:14]2)[CH2:12][CH2:11]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][CH:10]1[CH2:11][CH2:12][C:13](=[O:14])[CH2:18][CH2:19]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 103780318-(Benzyloxymethyl)-1,4-dioxaspiro[4.5]decane

Product 1

HCID 10443381Cyclohexanone, 4-[(phenylmethoxy)methyl]-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of crude 8-benzyloxymethyl-1,4-dioxa-spiro[4.5]decane (297 g) in THF (600 mL) is added 3N HCl (900 mL) at room temperature, and the mixture is stirred overnight. After addition of sat. NaHCO3 aq., the mixture is extracted with EtOAc. The water layer is extracted with EtOAc, 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-benzyloxymethylcyclohexanone.

Workup

  1. extractionthe mixture is extracted with EtOAc
  2. extractionThe water layer is extracted with EtOAc
  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-fb03e4e2c7bd4010b9f2751e3c9cb721
Source dataset
uspto-grants-2013_04
Patent number
US08410275B2

Reaction notes

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