Propionyl chloride → 1-Methyl-4-methylene-6-propionyloxy-2,3,3a,4,5,6,7,8-octahydroazulene

HRID 597345Notes

Reaction equation

HRID 597345 reaction equation
[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](Cl)(=[O:17])[CH2:15][CH3:16]>N1C=CC=CC=1.C(Cl)Cl>[CH3:12][C:8]1[CH2:7][CH2:6][CH:5]2[C:9]=1[CH2:10][CH2:11][CH:2]([O:1][C:14](=[O:17])[CH2:15][CH3:16])[CH2:3][C:4]2=[CH2:13]

Participants

5

Reactant 2

HCID 62324Propionyl chlorideHCID 214348863-Methyl-8-methylidene-1,2,4,5,6,7,8,8a-octahydroazulen-6-ol

Product 1

HCID 214349101-Methyl-4-methylene-6-propionyloxy-2,3,3a,4,5,6,7,8-octahydroazuleneYield 96%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 2.5 g of 6-hydroxy-1-methyl-4-methylen-2,3,3a,4,5,6,7,8-octahydroazulene in 5 ml of pyridine and 50 ml of methylene chloride was treated at -10° with 1.73 ml of propionyl chloride. After 3 hours stirring, the solution was poured on to ice and worked up in a conventional manner. After distillation of the crude produce under high vacuum, there were obtained 3.15 g (96%) of pure 1-methyl-4-methylene-6-propionyloxy-2,3,3a,4,5,6,7,8-octahydroazulene; b.p0.05 65°-70°; IR(film): νmax = 1380, 1730, 1640, 1460, 1440, 1375, 1340, 1270, 1190, 1158, 1080, 1018, 895 cm- 1. The compound has a woody, spicy, balsamic, slightly earthy odour.

Workup

  1. additionthe solution was poured on to ice
  2. distillationAfter distillation of the crude
  3. customproduce under high vacuum

Sources & evidence

ORD record
ord-ee52e327a0f44b20a7d25d9cbdc34a1d
Source dataset
uspto-grants-1977_03
Patent number
US04013726

Reaction notes

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