Toluene → 4-Hydroxy-4-methylpentyl 5-norbornene-2-carboxylate

HRID 1835965

Reaktionsgleichung

Reaktionsgleichung von HRID 1835965
[CH3:1][C:2]([OH:8])([CH3:7])[CH2:3][CH2:4][CH2:5][OH:6].C(N(CC)CC)C.C1(C)C=CC=CC=1.[CH:23]12[CH2:29][CH:26]([CH:27]=[CH:28]1)[CH2:25][CH:24]2[C:30](Cl)=[O:31]>O>[CH:23]12[CH2:29][CH:26]([CH:27]=[CH:28]1)[CH2:25][CH:24]2[C:30]([O:6][CH2:5][CH2:4][CH2:3][C:2]([OH:8])([CH3:7])[CH3:1])=[O:31]

Komponenten

6

Edukt 4

HCID 1140TolueneHCID 8471TriethylamineHCID 98233Bicyclo(2.2.1)hept-5-ene-2-carbonyl chlorideHCID 109862004-Methylpentane-1,4-diol

Produkt 1

HCID 221790144-Hydroxy-4-methylpentyl 5-norbornene-2-carboxylateAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a mixture of 118 g of 4-methyl-1,4-pentanediol, 111 g of triethylamine and 400 ml of toluene at 20° C., 157 g of 5-norbornene-2-carbonyl chloride was added over one hour. After 5 hours of stirring, 200 ml of water was added to the reaction solution to stop the reaction whereupon the mixture separated. The organic layer was washed with water and saturated sodium chloride water, dried over anhydrous sodium sulfate, and concentrated in vacuum. It was purified by vacuum distillation, collecting 214 g of 4-hydroxy-4-methylpentyl 5-norbornene-2-carboxylate (boiling point: 111-113° C./27 Pa, yield: 90%).

Aufarbeitung

  1. customthe reaction whereupon the mixture
  2. customseparated
  3. washThe organic layer was washed with water and saturated sodium chloride water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuum
  6. distillationIt was purified by vacuum distillation

Quellen und Nachweise

ORD-Eintrag
ord-aa6c6d5e8dab4bb08ea3b27ae5f825cf
Quelldatensatz
uspto-grants-2004_08
Patentnummer
US06774258B2

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