Dodecanoyl chloride → Geranyl laurate

HRID 266666ノート

反応式

HRID 266666 の反応式
[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]

参加物

6

反応物 4

HCID 8166Dodecanoyl chlorideHCID 8471TriethylamineHCID 637566GeraniolHCID 643820Nerol

生成物 1

HCID 6114709Geranyl laurate

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-7e6b6ea7f27d44c9954dbe7c9a6d970f
出典データセット
uspto-grants-1997_07
特許番号
US05652205

反応ノート

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