1-Iodo-trans-1-octene-3-ol → 1-Iodo-3-(p-anisyldiphenylmethoxy)-trans-1-octene

HRID 225369Notes

Reaction equation

HRID 225369 reaction equation
[I:1]/[CH:2]=[CH:3]/[CH:4]([OH:10])[CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[CH2:11]([C:20](Cl)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1>N1C=CC=CC=1>[I:1]/[CH:2]=[CH:3]/[CH:4]([O:10][C:20]([CH2:11][C:12]1[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

4

Reactant 2

HCID 110432831-Iodo-trans-1-octene-3-olHCID 14836583p-Anisyldiphenylmethyl chloride

Product 1

HCID 201446231-Iodo-3-(p-anisyldiphenylmethoxy)-trans-1-octene

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 14.92 g. (0.0588 mole) of 1-iodo-trans-1-octen-3-ol (Example 225) and 18.2 g. (0.0588 mole) of p-anisyldiphenylmethyl chloride in 165 ml. of dry pyridine is heated at 60° C. for 18 hours under an inert atmosphere. The mixture is cooled and the solvent is evaporated in vacuo. The residue is partitioned between ether and water, and the organic phase is washed with water and saturated brine, dried (MgSO4), and evaporated. The residue is chromatographed upon 300 g. of Florisil® packed in hexane and the product is eluted with hexane and 4:1 hexane-benzene to yield a colorless oil.

Workup

  1. additionA mixture of 14.92 g
  2. temperatureThe mixture is cooled
  3. customthe solvent is evaporated in vacuo
  4. customThe residue is partitioned between ether and water
  5. washthe organic phase is washed with water and saturated brine
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customThe residue is chromatographed upon 300 g
  9. washthe product is eluted with hexane and 4:1 hexane-benzene
  10. customto yield a colorless oil

Sources & evidence

ORD record
ord-3664a7bed06e4507991c3c2c81c1ade6
Source dataset
uspto-grants-1980_11
Patent number
US04236027

Reaction notes

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