Hydrochloric Acid → 7-Hydroxymethyl-7-methyl-1,4-dioxaspiro[4.5]decan-8-one

HRID 2068872Notes

Reaction equation

HRID 2068872 reaction equation
[CH3:1][CH:2]1[C:11](=[O:12])[CH2:10][CH2:9][C:4]2([O:8][CH2:7][CH2:6][O:5]2)[CH2:3]1.[CH2:13]=[O:14].Cl.[Cl-].[NH4+]>[OH-].[K+].CO>[OH:14][CH2:13][C:2]1([CH3:1])[C:11](=[O:12])[CH2:10][CH2:9][C:4]2([O:5][CH2:6][CH2:7][O:8]2)[CH2:3]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 25517Ammonium ChlorideHCID 2706287-Methyl-1,4-dioxaspiro[4.5]decan-8-one

Product 1

HCID 450966867-Hydroxymethyl-7-methyl-1,4-dioxaspiro[4.5]decan-8-oneYield 56%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14797Potassium HydroxideSolvent

Procedure

7-Methyl-1,4-dioxaspiro[4.5]decan-8-one (10.5 g, 62 mmol) was dissolved in methanolic potassium hydroxide solution (10 w/w %, 60 g). To the solution was added dropwise a solution of aqueous formaldehyde solution (37%, 4.6 ml) in methanol (5 ml) under ice-cooling over 20 min, and the mixture was stirred for 30 min. Then, to the reaction mixture were added 1 N hydrochloric acid and saturated aqueous ammonium chloride solution, and the mixture was extracted three times with chloroform. The combined organic layers were dried over magnesium sulfate. Magnesium sulfate was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography to give the title compound (6.9 g, yield 56%).

Workup

  1. temperaturecooling over 20 min
  2. extractionthe mixture was extracted three times with chloroform
  3. dry with materialThe combined organic layers were dried over magnesium sulfate
  4. customMagnesium sulfate was removed by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-41933ecaff9348479ca82bd519ba3396
Source dataset
uspto-grants-2012_10
Patent number
US08299070B2

Reaction notes

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