Pentaerythritol → Mono-o-(phytanyl)pentaerythritol

HRID 2260955

反応式

HRID 2260955 の反応式
[OH:1][CH2:2][C:3]([CH2:8][OH:9])([CH2:6][OH:7])[CH2:4][OH:5].[H-].[Na+].S(C1C=CC(C)=CC=1)(O[CH2:16][CH2:17][CH:18]([CH2:20][CH2:21][CH2:22][CH:23]([CH2:25][CH2:26][CH2:27][CH:28]([CH2:30][CH2:31][CH2:32][CH:33]([CH3:35])[CH3:34])[CH3:29])[CH3:24])[CH3:19])(=O)=O>CN(C=O)C>[CH3:19][CH:18]([CH2:20][CH2:21][CH2:22][CH:23]([CH3:24])[CH2:25][CH2:26][CH2:27][CH:28]([CH3:29])[CH2:30][CH2:31][CH2:32][CH:33]([CH3:35])[CH3:34])[CH2:17][CH2:16][O:1][CH2:2][C:3]([CH2:8][OH:9])([CH2:6][OH:7])[CH2:4][OH:5]

参加物

5

反応物 3

HCID 8285PentaerythritolHCID 24758Sodium hydrideHCID 201861853,7,11,15-Tetramethyl-1-hexadecanol 4-Methylbenzenesulfonate

生成物 1

HCID 11697364Mono-o-(phytanyl)pentaerythritol収率 22.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Under a nitrogen gas stream, 36.09 g (265.1 mmol) of pentaerythritol was dissolved in 210 ml of dry DMF, and 5.3 g (132.5 mmol) of 60% NaH was added little by little under ice cooling. The resultant was heated to room temperature and agitated for 1 hour, and 30.0 g (66.26 mmol) of phytanyl tosylate was added dropwise thereto, followed by washing with 55 ml of DMF. The resultant was heated to 80° C. and agitated for 4 hours, the resulting reaction solution was concentrated under reduced pressure, 500 ml of ether was added to the residual solution to perform extractive dissolution twice, the product was washed twice with saturated saline, and then it was dried over anhydrous magnesium sulfate. After the filtration, the resultant was concentrated, purified by silica gel column chromatography to obtain 6.3 g of mono-O-(3,7,11,15-tetramethylhexadecyl)pentaerythritol, which was in colorless, transparent, and somewhat viscous liquid form. The purity of the product determined by HPLC analysis was not lower than 99.5%. The results of NMR analysis are as shown below.

後処理

  1. washby washing with 55 ml of DMF
  2. temperatureThe resultant was heated to 80° C.
  3. stirringagitated for 4 hours
  4. customthe resulting reaction solution
  5. concentrationwas concentrated under reduced pressure, 500 ml of ether
  6. additionwas added to the residual solution
  7. dissolutiondissolution twice
  8. washthe product was washed twice with saturated saline
  9. dry with materialit was dried over anhydrous magnesium sulfate
  10. filtrationAfter the filtration
  11. concentrationthe resultant was concentrated
  12. custompurified by silica gel column chromatography

出典と根拠

ORDレコード
ord-49d880234d514920815a94701b30ce55
出典データセット
uspto-grants-2010_12
特許番号
US07846903B2

関連ノート

読み込み中…