Methyl bicyclo[2.2.1]hept-5-ene-2-carboxylate → 4-Hydroxy-4-methylpentyl 5-norbornene-2-carboxylate

HRID 1795732Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1795732
[CH3:1][C:2]([OH:8])([CH3:7])[CH2:3][CH2:4][CH2:5][OH:6].[CH:9]12[CH2:15][CH:12]([CH:13]=[CH:14]1)[CH2:11][CH:10]2[C:16](OC)=[O:17]>C[O-].[Na+].C1(C)C=CC=CC=1>[CH:9]12[CH2:15][CH:12]([CH:13]=[CH:14]1)[CH2:11][CH:10]2[C:16]([O:6][CH2:5][CH2:4][CH2:3][C:2]([OH:8])([CH3:7])[CH3:1])=[O:17]

Komponenten

5

Edukt 2

HCID 250075Methyl bicyclo[2.2.1]hept-5-ene-2-carboxylateHCID 109862004-Methylpentane-1,4-diol

Produkt 1

HCID 221790144-Hydroxy-4-methylpentyl 5-norbornene-2-carboxylateAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 10942334Sodium MethoxideKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 118 g of 4-methyl-1,4-pentanediol, 173 g of methyl 5-norbornene-2-carboxylate, 1.4 g of sodium methoxide and 400 ml of toluene was heated under reflux for 5 hours while distilling off the methanol which formed during the reaction. The reaction solution was cooled, washed with saturated sodium bicarbonate water, dried over anhydrous sodium sulfate, and concentrated in vacuum. It was purified by vacuum distillation, collecting 221 g of 4-hydroxy-4-methylpentyl 5-norbornene-2-carboxylate (yield: 93%). The physical data of this product were in good coincidence with those of Synthesis Example 1.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 5 hours
  3. distillationwhile distilling off the methanol which
  4. customformed during the reaction
  5. temperatureThe reaction solution was cooled
  6. washwashed with saturated sodium bicarbonate water
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated in vacuum
  9. distillationIt was purified by vacuum distillation

Quellen und Nachweise

ORD-Eintrag
ord-93e6cc7cbf4745f3b78dda48a9e3b2d9
Quelldatensatz
uspto-grants-2006_04
Patentnummer
US07029822B2

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