Ammonium Chloride → 9-Benzyl-3,3-dimethyl-1,5-dioxaspiro[5.5]undecan-9-ol

HRID 1485085

Reaction equation

HRID 1485085 reaction equation
[CH3:1][C:2]1([CH3:14])[CH2:13][O:12][C:5]2([CH2:11][CH2:10][C:8](=[O:9])[CH2:7][CH2:6]2)[O:4][CH2:3]1.[Cl-].[NH4+].[CH2:17]([Mg]Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>O1CCCC1.[Cl-].[Zn+2].[Cl-]>[CH2:17]([C:8]1([OH:9])[CH2:7][CH2:6][C:5]2([O:4][CH2:3][C:2]([CH3:14])([CH3:1])[CH2:13][O:12]2)[CH2:11][CH2:10]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 5879683,3-Dimethyl-1,5-dioxaspiro(5.5)undecan-9-oneHCID 178419663HCID 178419663, compound

Product 1

HCID 1181131779-Benzyl-3,3-dimethyl-1,5-dioxaspiro[5.5]undecan-9-ol

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1,4-cyclohexanedione mono-2,2-dimethyltrimethylene ketal (3.76 g) and zinc chloride (about 1.0 mol/L, solution in diethyl ether, 1.90 mL) in tetrahydrofuran (63.0 mL), benzylmagnesium bromide (about 1.0 mol/L, solution in tetrahydrofuran, 24.7 mL) was added at 0° C. and thereafter the mixture was stirred at that temperature for 2.5 hours. To the reaction mixture, a saturated aqueous solution of ammonium chloride was added and three extractions were conducted with ethyl acetate. The combined organic layers were washed with saturated brine and thereafter dried over anhydrous magnesium sulfate. The desiccant was removed by filtration and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=95:5-60:40) to give 9-benzyl-3,3-dimethyl-1,5-dioxaspiro[5.5]undecan-9-ol as a colorless solid (1.28 g).

Workup

  1. extractionthree extractions
  2. washThe combined organic layers were washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe desiccant was removed by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=95:5-60:40)

Sources & evidence

ORD record
ord-cf3c8959c6b94260993dd2e3d49cdada
Source dataset
uspto-grants-2016_08
Patent number
US09422240B2

Linked notes

Loading…