Sulfuric Acid → 3-(Tert-butoxy)-1-iodohexane

HRID 436090ノート

反応式

HRID 436090 の反応式
ClCCC(O)CCC.[I-].[Na+].[I:11][CH2:12][CH2:13][CH:14]([OH:18])[CH2:15][CH2:16][CH3:17].S(=O)(=O)(O)O.[CH3:24][C:25](=[CH2:27])[CH3:26]>C(Cl)Cl.CC(=O)CC>[C:25]([O:18][CH:14]([CH2:15][CH2:16][CH3:17])[CH2:13][CH2:12][I:11])([CH3:27])([CH3:26])[CH3:24]

参加物

8

反応物 5

HCID 1118Sulfuric AcidHCID 5238Sodium IodideHCID 8255IsobutyleneHCID 189210041-Iodohexan-3-OLHCID 189210071-Chlorohexan-3-ol

生成物 1

HCID 204656183-(Tert-butoxy)-1-iodohexane

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 6569Methyl Ethyl Ketone溶媒

実験手順

A mixture of 23.4 g. of 1-chloro-3-hexanol [Fourneau, et. al., Bull. Soc. Chem. France, 25, 367 (1919)] in 300 ml. of 2-butanone containing 30 g. of sodium iodide is stirred at the reflux temperature for 18 hours. The cooled solution is filtered and the mother liquor is taken to dryness. Distillation of the residue affords 32.9 g. (84%) of 1-iodo-3-hexanol, b.p. 105° C. (10 mm). Treatment of this material in 500 ml. of methylene chloride, containing 4 ml. of concentrated sulfuric acid, with isobutylene according to the procedure described in Example 492 gives 27 g. of crude material. Chromatography on florisil affords 16 g. of product; μ max. 7.22 and 7.37 μ (tert-butyl group).

後処理

  1. additionA mixture of 23.4 g
  2. filtrationThe cooled solution is filtered
  3. distillationDistillation of the residue
  4. customaffords 32.9 g
  5. customgives 27 g
  6. customChromatography on florisil affords 16 g

出典と根拠

ORDレコード
ord-1fd9f8979d5048e9b341418b4ae957f4
出典データセット
uspto-grants-1977_02
特許番号
US04007210

反応ノート

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