N,N-Dimethylaniline → 1-Oxaspiro[4.5]decan-6-ol, 2,6,10,10-tetramethyl-, 6-acetate

HRID 1112080Notes

Reaction equation

HRID 1112080 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[CH3:5][CH:6]1[CH2:10][CH2:9][C:8]2([C:15]([CH3:17])([CH3:16])[CH2:14][CH2:13][CH2:12][C:11]2([CH3:19])[OH:18])[O:7]1.CN(C)C1C=CC=CC=1.OS(O)(=O)=O>CCOCC>[C:1]([O:18][C:11]1([CH3:19])[CH2:12][CH2:13][CH2:14][C:15]([CH3:17])([CH3:16])[C:8]21[O:7][CH:6]([CH3:5])[CH2:10][CH2:9]2)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 949N,N-DimethylanilineHCID 1118Sulfuric AcidHCID 6367Acetyl chlorideHCID 6542853398-90-6

Product 1

HCID 938381-Oxaspiro[4.5]decan-6-ol, 2,6,10,10-tetramethyl-, 6-acetate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

5.9 g (0.079 M) of acetyl chloride were added over 30 minutes at 20° to a mixture of 2,6,10,10-tetramethyl-1-oxa-spiro[4.5]decan-6-ol -- isomer A; see Example 1 -- and 10.9 g of N,N-dimethylaniline. After having been kept for 2 days at room temperature the reaction mixture was heated to reflux during 3 hours, then cooled and treated with 50 ml of ether. The reaction mixture was then filtered and the clear filtrate thus obtained poured onto crushed ice and finally acidified with a 10% aqueous solution of H2SO4. The organic layer was then washed with NaHCO3 in water, dried, evaporated and subjected to a fractional distillation to give 2.5 g of a product having b.p. 90°-100°/0.1 Torr. After crystallisation in aqueous ethanol 1.9 g (75%) of the desired ester were isolated -- isomer A --.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux during 3 hours
  3. temperaturecooled
  4. filtrationThe reaction mixture was then filtered
  5. customthe clear filtrate thus obtained
  6. additionpoured
  7. customonto crushed ice
  8. washThe organic layer was then washed with NaHCO3 in water
  9. customdried
  10. customevaporated
  11. distillationsubjected to a fractional distillation

Sources & evidence

ORD record
ord-00e77e513dac4d998015914f2adcd428
Source dataset
uspto-grants-1978_10
Patent number
US04120830

Reaction notes

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