p-Toluenesulfonic acid → 1-Oxaspiro[4.5]dec-7-ene

HRID 1903763ノート

反応式

HRID 1903763 の反応式
[C:1]1([CH2:7][CH2:8][CH2:9][OH:10])[CH2:6][CH:5]=[CH:4][CH2:3][CH:2]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>O>[O:10]1[C:1]2([CH2:6][CH2:5][CH:4]=[CH:3][CH2:2]2)[CH2:7][CH2:8][CH2:9]1

参加物

4

反応物 2

HCID 6101p-Toluenesulfonic acidHCID 20402847HCID 20402847、化合物

生成物 1

HCID 132984301-Oxaspiro[4.5]dec-7-ene収率 76%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
115 °C

実験手順

This crude 3-(1,4-cyclohexadienyl)propan-1-ol thus obtained was divided into two batches. Each batch was treated separately with 2.5 g of p-toluenesulfonic acid. The pressure was lowered to 12 mmHg and the pot immersed in an oil bath heated to 115° C. After about 0.3 hr distillation through a short vacuum jacketed vigreaux column at reduced pressure began and continued at a steady rate as cyclization proceeded. A total of 105.4 g (76% yield) of the 1-oxaspiro[4.5]dec-7-ene was obtained as a water white liquid, bp 79°-81° C. (12 mmHg). The NMR spectrum was identical to that for the same compound described in Example 1 above, step E.

後処理

  1. customthe pot immersed in an oil bath
  2. distillationAfter about 0.3 hr distillation through a short vacuum

出典と根拠

ORDレコード
ord-585a680b1e564fc5809a24281ca2d56d
出典データセット
uspto-grants-1984_03
特許番号
US04438130

反応ノート

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