Hydrochloric Acid → 1-Cyclohexyloxy-2,2,6,6-tetramethyl-piperidin-4-ol

HRID 133660

反応式

HRID 133660 の反応式
[OH:1][N:2]1[C:7]([CH3:9])([CH3:8])[CH2:6][CH:5]([OH:10])[CH2:4][C:3]1([CH3:12])[CH3:11].[C:13](#N)[CH3:14].Cl.OO>O.[Fe].C1CCCCC1>[CH:14]1([O:1][N:2]2[C:7]([CH3:8])([CH3:9])[CH2:6][CH:5]([OH:10])[CH2:4][C:3]2([CH3:12])[CH3:11])[CH2:13][CH2:5][CH2:4][CH2:3][CH2:11]1

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 53951,4-Dihydroxy-2,2,6,6-tetramethylpiperidineHCID 6342Acetonitrile

生成物 1

HCID 113228111-Cyclohexyloxy-2,2,6,6-tetramethyl-piperidin-4-ol収率 75%

試薬・触媒・溶媒 3

HCID 23925Iron触媒HCID 962Water溶媒HCID 8078Cyclohexane溶媒

実験手順

Nanosized activated iron powder in mineral oil (0.042 g) is rinsed successively with two 2 ml portions of cyclohexane. Most of the solvent is removed with a pipette. The iron is added to a mixture of 5.00 g (29.0 mmol) of 1-oxyl-2,2,6,6-tetramethylpiperidin-4-ol, 44 ml of acetonitrile, and 32 ml of cyclohexane that has been heated to 40 degrees. To this mixture is carefully added over several minutes a solution of 0.548 g of concentrated hydrochloric acid in 3 ml of water. The reaction temperature is brought to reflux and a solution of 7.81 g (115 mmol) of 50% aqueous hydrogen peroxide is added dropwise over a period of 2.25 hours. After about one-half of the peroxide solution is added, a second portion of nanosized activated iron powder in mineral oil (0.039 g), rinsed twice with cyclohexane, and a solution of 0.166 g of concentrated hydrochloric acid in 1 ml of water are added to the reaction mixture. The reaction mixture is heated at 60-62 degrees for 1.5 hours after the peroxide has been added. After work up and purification according to the procedure of Example 54, the yield of the title compound is 5.53 g (75% yield), GC assay 96%.

後処理

  1. washNanosized activated iron powder in mineral oil (0.042 g) is rinsed successively with two 2 ml portions of cyclohexane
  2. customMost of the solvent is removed with a pipette
  3. temperaturehas been heated to 40 degrees
  4. temperatureto reflux
  5. washa second portion of nanosized activated iron powder in mineral oil (0.039 g), rinsed twice with cyclohexane
  6. additiona solution of 0.166 g of concentrated hydrochloric acid in 1 ml of water are added to the reaction mixture
  7. temperatureThe reaction mixture is heated at 60-62 degrees for 1.5 hours after the peroxide
  8. additionhas been added
  9. customAfter work up and purification

出典と根拠

ORDレコード
ord-8cc8f4924bc947049035d8086d40e92b
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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