Acetyl chloride → 6-Acetoxy-1,6-dimethyl-4-methylen-2,3,3a,4,5,6,7,8-octahydroazulene

HRID 597347Notes

Reaction equation

HRID 597347 reaction equation
[OH:1][C:2]1([CH3:14])[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:15](Cl)(=[O:17])[CH3:16]>N1C=CC=CC=1.C(Cl)Cl>[C:15]([O:1][C:2]1([CH3:14])[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:17])[CH3:16]

Participants

5

Reactant 2

HCID 6367Acetyl chlorideHCID 214348993,6-Dimethyl-8-methylidene-1,2,4,5,6,7,8,8a-octahydroazulen-6-ol

Product 1

HCID 214349136-Acetoxy-1,6-dimethyl-4-methylen-2,3,3a,4,5,6,7,8-octahydroazulene

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 2.0 g of 6-hydroxy-1,6-dimethyl-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 1.1 ml of acetyl chloride. The mixture was left to stand overnight at room temperature, then poured on to ice and worked up in a conventional manner. The crude product (3.1 g) which was obtained in the form of a brown oil, was chromatographed on 50 times the amount of silica gel. By elution with hexane/ether (19:1) there was obtained pure 6-acetoxy-1,6-dimethyl-4-methylen-2,3,3a,4,5,6,7,8-octahydroazulene; b.p.0.01 ca 70°; IR(film):νmax = 3090, 1735, 1640, 1445, 1368, 1270/50/30, 1095, 1065, 1020, 905/900 cm- 1. The compound has a flowery odour with a woody undertone.

Workup

  1. waitThe mixture was left
  2. additionpoured on to ice
  3. customThe crude product (3.1 g) which was obtained in the form of a brown oil
  4. customwas chromatographed on 50 times the amount of silica gel
  5. washBy elution with hexane/ether (19:1) there

Sources & evidence

ORD record
ord-73ef6ed3ed5740fea1ed5e57ff0f64b3
Source dataset
uspto-grants-1977_03
Patent number
US04013726

Reaction notes

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