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

HRID 1580391Notes

Reaction equation

HRID 1580391 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>>[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

3

Reactant 2

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

Product 1

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

Conditions

Temperature
60 °C

Procedure

A mixture of 14.92 g. (0.0588 mole) of 1-iodo-trans-1-octen-3-ol (Example 955) and 18.2 g. (0.0588 mole) of p-anisyldiphenylmethyl chloride in 165 ml. of dry pryidine 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 the 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 the
  10. customyield a colorless oil

Sources & evidence

ORD record
ord-d4d39a839007443a8fe1660f05b453b2
Source dataset
uspto-grants-1976_01
Patent number
US03932479

Reaction notes

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