Ammonium Chloride → 1,4-Dioxaspiro(4.5)decane-8-carbaldehyde

HRID 1743738Notes

Reaction equation

HRID 1743738 reaction equation
C([C:3]1([C:13]([O-])=[O:14])[CH2:8][CH2:7][C:6]2([O:12][CH2:11][CH2:10][O:9]2)[CH2:5][CH2:4]1)C.[H-].C([Al+]CC(C)C)C(C)C.[Cl-].[NH4+]>C1(C)C=CC=CC=1>[CH2:11]1[CH2:10][O:9][C:6]2([CH2:5][CH2:4][CH:3]([CH:13]=[O:14])[CH2:8][CH2:7]2)[O:12]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 21225700DiisobutylaluminumhydrideHCID 22236514HCID 22236514, compound

Product 1

HCID 98989471,4-Dioxaspiro(4.5)decane-8-carbaldehydeYield 87%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

214 mg (1 mmol) of ethyl-4,4-(ethylenedioxy)cyclohexanecarboxylate is cooled in 15 ml of toluene under argon and in a moisture-free environment to −78° C., and it is mixed drop by drop with 0.85 ml of a 1.2 molar solution of diisobutyl aluminum hydride (DIBAH) in toluene. After 15 minutes of stirring at this temperature, it is mixed with about 10 ml of a saturated ammonium chloride solution. The organic phase is separated, washed with saturated common salt solution, dried, filtered and concentrated by evaporation. 148 mg (85% of theory) of 4,4-(ethylenedioxy)cyclohexane carbaldehyde is obtained.

Workup

  1. customThe organic phase is separated
  2. washwashed with saturated common salt solution
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-98a4e7cc75fc49e4b376a0632331e8d3
Source dataset
uspto-grants-2006_03
Patent number
US07012081B2

Reaction notes

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