Hydrochloric Acid → Cyclohexanone, 2-[(phenylmethoxy)methyl]-

HRID 1748171Notes

Reaction equation

HRID 1748171 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]1[CH2:19][CH2:18][CH2:17][CH2:16][C:11]21OCC[O:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C(=O)([O-])[O-].[Na+].[Na+]>CC(C)=O>[CH2:1]([O:8][CH2:9][CH:10]1[CH2:19][CH2:18][CH2:17][CH2:16][C:11]1=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 686237586-((Benzyloxy)methyl)-1,4-dioxaspiro[4.5]decane

Product 1

HCID 10489011Cyclohexanone, 2-[(phenylmethoxy)methyl]-

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 6-((Benzyloxy)methyl)-1,4-dioxaspiro[4.5]decane (2.4 g 9.1 mmol) in acetone (40 mL) was treated with 1.5N HCl (18 mL) and stirred at rt for 5 hours. The reaction mixture was neutralized with aqueous sodium carbonate and the volatile removed in vacuo. The residue was extracted with Et2O (3×50 mL) and the combined organic layer were washed with water (30 mL), brine (30 mL) and dried over sodium sulfate and concentrated to yield the desired product as pale yellow oil that was used in the next step without further purification. MS m/z 219.1 (M+1).

Workup

  1. customthe volatile removed in vacuo
  2. extractionThe residue was extracted with Et2O (3×50 mL)
  3. washthe combined organic layer were washed with water (30 mL), brine (30 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5c7a327edd30448b824639d9178071f1
Source dataset
uspto-grants-2015_10
Patent number
US09150568B2

Reaction notes

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