Octane → Tinuvin 123

HRID 133638

反応式

HRID 133638 の反応式
[C:1]([O:25][CH:26]1[CH2:31][C:30]([CH3:33])([CH3:32])[N:29]([OH:34])[C:28]([CH3:36])([CH3:35])[CH2:27]1)(=[O:24])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([O:12][CH:13]1[CH2:18][C:17]([CH3:20])([CH3:19])[N:16]([OH:21])[C:15]([CH3:23])([CH3:22])[CH2:14]1)=[O:11].[CH3:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44].OO.S([O-])([O-])=O.[Na+].[Na+]>O.C(O)(=O)C.C(#N)C>[C:1]([O:25][CH:26]1[CH2:27][C:28]([CH3:36])([CH3:35])[N:29]([O:34][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[C:30]([CH3:33])([CH3:32])[CH2:31]1)(=[O:24])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([O:12][CH:13]1[CH2:14][C:15]([CH3:22])([CH3:23])[N:16]([O:21][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])[C:17]([CH3:19])([CH3:20])[CH2:18]1)=[O:11]

参加物

8

反応物 4

HCID 356OctaneHCID 784Hydrogen PeroxideHCID 24437Sodium SulfiteHCID 11272241Bis(1-hydroxy-2,2,6,6-tetramethyl-4-piperidinyl)decandioate

生成物 1

HCID 3592789Tinuvin 123収率 31%

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒3 回HCID 962Water溶媒3 回HCID 6342Acetonitrile溶媒

反応条件

温度
76 °C

実験手順

A solution of 0.308 g (1.14 g) of ferric chloride hexahydrate and 0.225 g (3.75 mmol) of glacial acetic acid in 5 ml of water is added to a mixture of 10.00 g (19.6 mmol) of bis(1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl) sebacate, 94 ml of acetonitrile, and 64 ml of n-octane that is heated to 76° C. The reaction mixture is kept at the reflux temperature of 76° as a solution of 11.52 g (169 mmol) of 50% aqueous hydrogen peroxide is added dropwise over 3 hours. A solution of 0.106 g of ferric chloride hexahydrate and 0.102 g of glacial acetic acid in 1.6 g of water is added to the reaction mixture 1.75 hours after the peroxide addition is begun. A solution of 0.106 g of ferric chloride hexahydrate and 0.073 g of glacial acetic acid in 1.6 g of water is added to the reaction mixture 2.75 hours after the peroxide addition is begun. The reaction mixture is maintained at the reflux temperature for 1 hour after the peroxide is added. Excess peroxide is decomposed by stirring the reaction mixture with aqueous sodium sulfite solution. Solids are removed by filtration. The aqueous layer of the filtrate is extracted with ethyl acetate. The combined organic layers are concentrated, and the concentrate is purified twice by flash chromatography with a 100:7.5 mixture of heptane-ethyl acetate to afford 4.43 g (31% yield) of the title compound, a colorless liquid. NMR analysis shows a mixture of octyl regioisomers.

後処理

  1. additionis added dropwise over 3 hours
  2. additionis added
  3. customSolids are removed by filtration
  4. extractionThe aqueous layer of the filtrate is extracted with ethyl acetate
  5. concentrationThe combined organic layers are concentrated
  6. customthe concentrate is purified twice by flash chromatography with a 100:7.5 mixture of heptane-ethyl acetate

出典と根拠

ORDレコード
ord-2ea7aa7d72964983a1f9433f940eb17b
出典データセット
uspto-grants-2008_06
特許番号
US07390904B2

関連ノート

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