Acetic Anhydride → 6-Formyloxy-1-methyl-4-methylen-2,3,3a,4,5,6,7,8-octahydroazulene

HRID 1581061Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1581061
[OH:1][CH:2]1[CH2:11][CH2:10][C:9]2[CH:5]([CH2:6][CH2:7][C:8]=2[CH3:12])[C:4](=[CH2:13])[CH2:3]1.[C:14](OC(=O)C)(=[O:16])C.C(=O)([O-])[O-].[Na+].[Na+]>N1C=CC=CC=1.C(O)=O>[CH:14]([O:1][CH:2]1[CH2:11][CH2:10][C:9]2[CH:5]([CH2:6][CH2:7][C:8]=2[CH3:12])[C:4](=[CH2:13])[CH2:3]1)=[O:16]

Komponenten

6

Edukt 3

HCID 7918Acetic AnhydrideHCID 10340Sodium CarbonateHCID 214348863-Methyl-8-methylidene-1,2,4,5,6,7,8,8a-octahydroazulen-6-ol

Produkt 1

HCID 214349086-Formyloxy-1-methyl-4-methylen-2,3,3a,4,5,6,7,8-octahydroazuleneAusbeute 87,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineKatalysatorHCID 284Formic AcidLösungsmittel

Versuchsvorschrift

2.67 g of 6-hydroxy-1-methyl-4-methylen-2,3,3a,4,5,6,7,8-octahydroazulene were treated at 0° firstly with half of a mixture of 4.08 g of acetic anhydride, 1.84 g of formic acid and 37 mg of pyridine. The mixture was stirred for 24 hours at room temperature and with exclusion of light. Then the other half of the reagent was added and the mixture stirred for further 24 hours. The solution was poured on to a mixture of ice and sodium carbonate and worked up in a conventional manner. The crude product so obtained (3.18 g) was distilled under high vacuum and yielded 2.70 g (87%) of pure 6-formyloxy-1-methyl-4-methylen-2,3,3a,4,5,6,7,8-octahydroazulene; b.p.0.005 50°; IR(film):νmax = 3120, 1728, 1645, 1460/45, 1190/82, 1015/1000, 905/900 cm-1. The compound smells woody, cedar-like, slightly ionone-like.

Aufarbeitung

  1. additionThen the other half of the reagent was added
  2. stirringthe mixture stirred for further 24 hours
  3. customThe crude product so obtained (3.18 g)
  4. distillationwas distilled under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-11843dc6b0c5490ea20412548708f7c8
Quelldatensatz
uspto-grants-1976_01
Patentnummer
US03935253

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