Pentaerythritol → Mono-o-(phytanyl)pentaerythritol

HRID 2260955

반응식

HRID 2260955 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 11697364Mono-o-(phytanyl)pentaerythritol수율 22.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-49d880234d514920815a94701b30ce55
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07846903B2

연결된 노트

불러오는 중…