Tetrahydrofuran → 2,6-Dimethyl-5-methylene-1-hepten-4-ol

HRID 64743ノート

反応式

HRID 64743 の反応式
[Mg].O1CCCC1.Cl[CH2:8][C:9]([CH3:11])=[CH2:10].[CH:12]([C:15](=[CH2:18])[CH:16]=[O:17])([CH3:14])[CH3:13]>C1(C)C=CC=CC=1>[CH3:11][C:9]([CH2:8][CH:16]([OH:17])[C:15](=[CH2:18])[CH:12]([CH3:14])[CH3:13])=[CH2:10]

参加物

6

反応物 4

HCID 8028TetrahydrofuranHCID 112413-Chloro-2-methyl-1-propeneHCID 781313-Methyl-2-methylenebutyraldehydeHCID 5462224Magnesium

生成物 1

HCID 202373802,6-Dimethyl-5-methylene-1-hepten-4-ol収率 73.8%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A mixture of magnesium turnings (146 grams) and tetrahydrofuran (2,000 grams) is heated to reflux with vigorous agitation. To this mixture is added a mixture of 3-chloro-2-methylpropene (500 grams), toluene (75 grams), and 3-methyl-2-methylenebutanal (500 grams prepared according to Example I), at such a rate as to maintain reflux. The addition requires approximately four hours. The mass is stirred at reflux for 30 minutes and is then cooled to room temperature and quenched into excess ice cold 10% aqueous acetic acid mixture. The organic layer is washed successively with an equal volume of water, saturated sodium carbonate solution and saturated salt solution. Rapid distillation at 3-12 mm/Hg pressure using a short column followed by careful redistillation (after bulking) through a 12"×1" Goodloe packed column yields 580 grams of 2,6-dimethyl-5-methylene-1-hepten-4-ol, boiling point range 73°-78° C. at 9 mm/Hg pressure.

後処理

  1. temperatureis heated
  2. temperatureto reflux with vigorous agitation
  3. additionTo this mixture is added
  4. temperatureat such a rate as to maintain
  5. temperaturereflux
  6. additionThe addition
  7. temperatureat reflux for 30 minutes
  8. customquenched into excess ice cold 10% aqueous acetic acid mixture
  9. washThe organic layer is washed successively with an equal volume of water, saturated sodium carbonate solution and saturated salt solution
  10. distillationRapid distillation at 3-12 mm/Hg pressure
  11. distillationfollowed by careful redistillation (after bulking) through a 12"×1"

出典と根拠

ORDレコード
ord-471e6649a09047e18a6480c0836ceb48
出典データセット
uspto-grants-1986_09
特許番号
US04609754

反応ノート

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