Iodine → HCID 22245625, compound

HRID 1729770Notes

Reaction equation

HRID 1729770 reaction equation
[Mg].[CH2:2](Br)[CH3:3].II.C(Cl)=C.[CH2:10]([CH:12]1[O:17][CH:16]([OH:18])[CH2:15][CH2:14][CH2:13]1)[CH3:11].[Cl-].[NH4+]>O1CCCC1>[OH:17][CH:12]([CH2:13][CH2:14][CH2:15][CH:16]([OH:18])[CH2:2][CH3:3])[CH:10]=[CH2:11]

Participants

9

Reactant 6

HCID 807IodineHCID 6332Ethyl BromideHCID 6338Vinyl ChlorideHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 12222759HCID 12222759, compound

Product 1

HCID 22245625HCID 22245625, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
30 °C

Procedure

To 7.6 grams of magnesium in 7 milliliters of anhydrous tetrahydrofuran containing a few drops of ethyl bromide and a few milligrams of iodine maintained at 45°-48°C. was added, over a 4-hour period, 120 milliliters of a 20.8 weight per cent solution of vinyl chloride in tetrahydrofuran. The resulting reaction mixture was cooled to 30°C. and a solution of 13 grams of 6-ethyl-2-hydroxytetrahydropyran in 40 milliliters of tetrahydrofuran was added. After standing overnight, there was added ice and ammonium chloride. Extraction of the resulting mixture with three 250-milliliter portions of ether, washing with three 100-milliliter portions of sodium chloride, drying over sodium sulfate, and evaporation gave 16 grams of 3,7-dihydroxy-1-nonene.

Workup

  1. additionwas added, over a 4-hour period
  2. customThe resulting reaction mixture
  3. extractionExtraction of the resulting mixture with three 250-milliliter portions of ether
  4. washwashing with three 100-milliliter portions of sodium chloride
  5. dry with materialdrying over sodium sulfate, and evaporation

Sources & evidence

ORD record
ord-68fa0009b42d4103a8e23780798e3953
Source dataset
uspto-grants-1976_11
Patent number
US03989724

Reaction notes

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