3-(3',5'-Di-tert-butyl-4'-hydroxyphenyl)propionic acid → HCID 21488283、化合物

HRID 1974010ノート

反応式

HRID 1974010 の反応式
O[CH:2]1[CH2:9][CH2:8][CH:7]([OH:10])[CH:6]2[N:11]([CH3:12])[CH:3]1[CH2:4][CH2:5]2.[C:13]([C:17]1[CH:18]=[C:19]([CH2:28][CH2:29][C:30]([OH:32])=[O:31])[CH:20]=[C:21]([C:24]([CH3:27])([CH3:26])[CH3:25])[C:22]=1[OH:23])([CH3:16])([CH3:15])[CH3:14]>C1(C)C(C)=CC=CC=1.CCOCC.[Ti]>[C:13]([C:17]1[CH:18]=[C:19]([CH2:28][CH2:29][C:30]([O:32][CH:3]2[CH2:4][CH2:5][CH:6]3[N:11]([CH3:12])[CH:2]2[CH2:9][CH2:8][CH:7]3[O:10][C:30](=[O:31])[CH2:29][CH2:28][C:19]2[CH:20]=[C:21]([C:24]([CH3:25])([CH3:27])[CH3:26])[C:22]([OH:23])=[C:17]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:18]=2)=[O:31])[CH:20]=[C:21]([C:24]([CH3:25])([CH3:26])[CH3:27])[C:22]=1[OH:23])([CH3:16])([CH3:14])[CH3:15]

参加物

6

反応物 2

HCID 883893-(3',5'-Di-tert-butyl-4'-hydroxyphenyl)propionic acidHCID 214882869-Methyl-9-azabicyclo[4.2.1]nonane-2,5-diol

生成物 1

HCID 21488283HCID 21488283、化合物収率 56.6%

試薬・触媒・溶媒 3

HCID 23963Titanium触媒HCID 3283Diethyl Ether溶媒HCID 7237O-Xylene溶媒

実験手順

In a nitrogen atmosphere a stirred mixture of the diol mixture 2,6-dihydroxy-9-methyl-9-azabicyclo[3.3.1]nonane and 2,5-dihydroxy-9-methyl-9-azabicyclo[4.2.1]nonane (4.28 g., 0.025 mole), 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid (15.3 g, 0.055 mole) and 0.7 ml of titanium tetraisopripylate in 100 ml of xylene was heated under reflux in a flask equipped with a Dean-Stark trap for 14 hours. The xylene was evaporated under reduced pressure and the residue thus obtained was dissolved in ether. The ether solution was washed with 5% aqueous sodium hydroxide and then water. The dried (Na2SO4) solution was evaporated under reduced pressure to give an oily residue which was crystallized from petroleum ether. Recrystallization from methanol gave 9.8 g (56.6%) of the title ester, m.p. 107°-109°.

後処理

  1. temperaturewas heated
  2. temperatureunder reflux in a flask
  3. customequipped with a Dean-Stark trap for 14 hours
  4. customThe xylene was evaporated under reduced pressure
  5. customthe residue thus obtained
  6. washThe ether solution was washed with 5% aqueous sodium hydroxide
  7. dry with materialThe dried (Na2SO4) solution
  8. customwas evaporated under reduced pressure
  9. customto give an oily residue which
  10. customwas crystallized from petroleum ether
  11. customRecrystallization from methanol

出典と根拠

ORDレコード
ord-e0f4042f88fe4b3d81609b12ab42ffdb
出典データセット
uspto-grants-1976_12
特許番号
US04000113

反応ノート

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