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

HRID 597323ノート

反応式

HRID 597323 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

HCID 214349086-Formyloxy-1-methyl-4-methylen-2,3,3a,4,5,6,7,8-octahydroazulene収率 87.4%

試薬・触媒・溶媒 2

HCID 1049Pyridine触媒HCID 284Formic Acid溶媒

実験手順

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 compouond smells woody, cedar-like, slightly ionone-like.

後処理

  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

出典と根拠

ORDレコード
ord-92e6f352a28a4f02833cb28c83b000d4
出典データセット
uspto-grants-1977_03
特許番号
US04013711

反応ノート

読み込み中…