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

HRID 66995Notes

Reaction equation

HRID 66995 reaction equation
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]

Participants

8

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

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; λmax. 7.22 and 7.37μ (tert-butyl group).

Workup

  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

Sources & evidence

ORD record
ord-e3172361428d4c2587f9a7581b7f186e
Source dataset
uspto-grants-1982_08
Patent number
US04343949

Reaction notes

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