Diethyl Ether → HCID 13298426, compound

HRID 1903761Notes

Reaction equation

HRID 1903761 reaction equation
[O:1]=[C:2]1[CH2:11][CH2:10][C:5]2([O:9][CH2:8][CH2:7][O:6]2)[CH2:4][CH2:3]1.[CH2:12]([O:14][CH2:15][CH3:16])[CH3:13]>O>[CH2:12]([O:14][CH:15]([O:1][CH2:2][CH2:3][CH2:4][C:2]1([OH:1])[CH2:11][CH2:10][C:5]2([O:6][CH2:7][CH2:8][O:9]2)[CH2:4][CH2:3]1)[CH3:16])[CH3:13]

Participants

4

Reactant 2

HCID 3283Diethyl EtherHCID 5674151,4-Dioxaspiro[4.5]decan-8-one

Product 1

HCID 13298426HCID 13298426, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To the above lithiated intermediate there was added dropwise a solution of 85.8 g (0.55 mol) of 8-oxo-1,4-dioxaspiro[4.5]decane in one liter of dry diethyl ether (fresh cans, as above) over a period of about 2.5 hr. The resulting reaction mixture was allowed to warm slowly to room temperature and then poured into two liters of ice cold half saturated ammonium chloride in water solution. The phases were separated and the aqueous phase was extracted with one liter of diethyl ether. The ether layers were combined and washed with brine solution, dried over sodium sulfate, and then the ether solvent was removed under reduced pressure to leave, after drying to 45° C. (0.25 mm.Hg) for 14 hours, 142.15 g of a light yellow oil, the above named decan-8-ol acetal intermediate, which was of sufficient purity to use in the next step. A small sample of the named oil was distilled at reduced pressure to obtain a purer material bp 135°-140° C. (0.01 mmHg). The nuclear magnetic resonance spectrum (using CDCl3 solvent), was consistent with the above named decan-8-ol acetal compound.

Workup

  1. customThe resulting reaction mixture
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted with one liter of diethyl ether
  4. washwashed with brine solution
  5. dry with materialdried over sodium sulfate
  6. customthe ether solvent was removed under reduced pressure
  7. customto leave
  8. customafter drying to 45° C. (0.25 mm.Hg) for 14 hours
  9. distillationA small sample of the named oil was distilled at reduced pressure

Sources & evidence

ORD record
ord-dab3a59c48db4bbda2d0350ca7e5b1af
Source dataset
uspto-grants-1984_03
Patent number
US04438130

Reaction notes

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