Benzoic Acid → 6-Octen-1-ol, 3,7-dimethyl-, 1-benzoate

HRID 129033

Reaktionsgleichung

Reaktionsgleichung von HRID 129033
[C:1]([OH:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:10][C:11](=[CH:13][CH2:14][CH2:15][CH:16]([CH2:18][CH2:19]O)[CH3:17])[CH3:12].S(=O)(=O)(O)O>O1CCCC1>[C:1]([O:9][CH2:19][CH2:18][CH:16]([CH3:17])[CH2:15][CH2:14][CH:13]=[C:11]([CH3:12])[CH3:10])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 243Benzoic AcidHCID 1118Sulfuric AcidHCID 8842Citronellol

Produkt 1

HCID 1120496-Octen-1-ol, 3,7-dimethyl-, 1-benzoateAusbeute 19 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of benzoic acid (14.6 g, 0.12 mol) and citronellol (15.6 g, 0.1 mol) in tetrahydrofuran (THF) was heated on a water bath for 4 hours after the addition of concentrated sulfuric acid. The reaction was monitored by thin layer chromatography (TLC), and when the reaction was over, the reaction mixture was quenched over ice/water, extracted with THF or methylene chloride, washed with 5% sodium hydrogen carbonate, and dried over magnesium sulfate. The reaction mixture was concentrated under vacuum and purified by open column chromatography to yield 4.95 g (yield: 19%) of a product having the following physical properties.

Aufarbeitung

  1. temperaturewas heated on a water bath for 4 hours
  2. customwas quenched over ice/water
  3. extractionextracted with THF or methylene chloride
  4. washwashed with 5% sodium hydrogen carbonate
  5. dry with materialdried over magnesium sulfate
  6. concentrationThe reaction mixture was concentrated under vacuum
  7. custompurified by open column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-8ae7a9d7e5bd4357bcac3e8e586515e5
Quelldatensatz
uspto-grants-1995_11
Patentnummer
US05466718

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