Acetic Acid → HCID 22463279, 화합물

HRID 133643노트

반응식

HRID 133643 반응식
[C:1](O)(=O)[CH3:2].[OH:5][N:6]1[C:11]([CH3:13])([CH3:12])[CH2:10][CH:9]([O:14][C:15](=[O:33])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH2:8][C:7]1([CH3:35])[CH3:34].OO.S([O-])([O-])=O.[Na+].[Na+]>O.C(O)(=O)C.C(#N)C.C1CCCCC1>[CH:2]1([O:5][N:6]2[C:11]([CH3:12])([CH3:13])[CH2:10][CH:9]([O:14][C:15](=[O:33])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH2:8][C:7]2([CH3:34])[CH3:35])[CH2:1][CH2:9][CH2:8][CH2:7][CH2:34]1

참가 물질

9

반응물 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 24437Sodium SulfiteHCID 580171Octadecanoic acid, 1-hydroxy-2,2,6,6-tetramethyl-4-piperidinyl ester

생성물 1

HCID 22463279HCID 22463279, 화합물수율 511.4%

시약·촉매·용매 4

HCID 176Acetic Acid촉매2회HCID 962Water용매3회HCID 6342Acetonitrile용매HCID 8078Cyclohexane용매

실험 절차

A solution of 0.116 g (0.429 mmol) of ferric chloride hexahydrate and 0.096 g (1.60 mmol) of glacial acetic acid in 2 ml of water is added to a mixture of 5.08 g (11.6 mmol) of 1-oxyl-4-octadecanoyloxy-2,2,6,6-tetramethylpiperidine, 40 ml of cyclohexane, and 60 ml of acetonitrile that has been heated to 60°. A solution of 3.36 g (49.4 mmol) of aqueous 50% hydrogen peroxide is added to the reaction mixture dropwise over 2.5 hours at the reflux temperature of 60-62°. A solution of 0.033 g of ferric chloride hexahydrate and 0.040 g of glacial acetic acid in 1 ml of water is added to the reaction mixture 1.5 hours after the peroxide addition is begun. A solution of 0.031 g of ferric chloride and 0.028 g of glacial acetic acid in 1 ml of water is added to the reaction mixture 4 hours after the peroxide addition is begun. After being heated a total of 5 hours at reflux temperature, the reaction mixture is cooled and excess peroxide is decomposed by the addition of aqueous sodium sulfite solution. The organic layer is concentrated and purified by flash chromatography with 20:1 heptane-ethyl acetate to afford 4.27 g (71% yield) of the title compound, a white solid, mp 42-46. The assay is approximately 90% by NMR integration.

후처리

  1. temperaturehas been heated to 60°
  2. temperatureAfter being heated a total of 5 hours
  3. temperatureat reflux temperature
  4. temperaturethe reaction mixture is cooled
  5. concentrationThe organic layer is concentrated
  6. custompurified by flash chromatography with 20:1 heptane-ethyl acetate

출처 및 근거

ORD 기록
ord-03fabe7367bb4a3fac05e2c7d131743d
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07390904B2

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