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

HRID 597613ノート

反応式

HRID 597613 の反応式
[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]

参加物

6

反応物 4

HCID 949N,N-DimethylanilineHCID 1118Sulfuric AcidHCID 6367Acetyl chlorideHCID 654286-Hydroxydihydrotheaspirane

生成物 1

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

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-faeb7ce7dbb7442484f5adf7898eb507
出典データセット
uspto-grants-1977_03
特許番号
US04014905

反応ノート

読み込み中…