Dodecanoyl chloride → Geranyl laurate

HRID 266666노트

반응식

HRID 266666 반응식
[CH3:1][C:2](=[CH:4][CH2:5][CH2:6]/[C:7](=[CH:9]/[CH2:10][OH:11])/[CH3:8])[CH3:3].OC/C=C(/C)\CCC=C(C)C.C(N(CC)CC)C.[C:30](Cl)(=[O:42])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41]>C1(C)C=CC=CC=1>[C:30]([O:11][CH2:10]/[CH:9]=[C:7](/[CH2:6][CH2:5][CH:4]=[C:2]([CH3:1])[CH3:3])\[CH3:8])(=[O:42])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41]

참가 물질

6

반응물 4

HCID 8166Dodecanoyl chlorideHCID 8471TriethylamineHCID 637566GeraniolHCID 643820Nerol

생성물 1

HCID 6114709Geranyl laurate

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A mixture of geraniol and nerol (approximately 70:30 by weight) in the amount of 50.00 g (0.324 mol) and triethylamine in the amount of 36.08 g (0.357 mol) are combined with 300 mL of toluene. The reaction mixture is heated to reflux and lauroyl chloride in the amount 70.92 g (0.324 mol) is added dropwise over 15 min. After heating for an additional 30 min, the product mixture is cooled to room temperature and filtered. The filtrate is washed three times with 100 mL of saturated NaHCO3, 100 mL of water, and dried over MgSO4. After filtration, the filtrate is concentrated by rotary evaporation followed by Kugelrohr distillation. Purity of the product is determined by thin layer chromatography and the structure confirmed by 13C and 1H NMR.

후처리

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux
  3. temperatureAfter heating for an additional 30 min
  4. filtrationfiltered
  5. washThe filtrate is washed three times with 100 mL of saturated NaHCO3, 100 mL of water
  6. dry with materialdried over MgSO4
  7. filtrationAfter filtration
  8. concentrationthe filtrate is concentrated by rotary evaporation
  9. distillationfollowed by Kugelrohr distillation

출처 및 근거

ORD 기록
ord-7e6b6ea7f27d44c9954dbe7c9a6d970f
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05652205

반응 노트

불러오는 중…