Chloride → 1'-Hydroxyestragole

HRID 1282922Notes

Reaction equation

HRID 1282922 reaction equation
[CH2:1](Br)[CH:2]=CC1C=CC=CC=1.[Cl-].[Mg].C(Br)=C.[CH3:16][O:17][C:18]1[CH:25]=[CH:24][C:21]([CH:22]=[O:23])=[CH:20][CH:19]=1.[Cl-].[NH4+]>C(OCC)C.O1CCCC1>[CH3:16][O:17][C:18]1[CH:25]=[CH:24][C:21]([CH:22]([OH:23])[CH:1]=[CH2:2])=[CH:20][CH:19]=1

Participants

9

Reactant 6

HCID 312ChlorideHCID 11641BromoetheneHCID 25517Ammonium ChlorideHCID 312444-MethoxybenzaldehydeHCID 98116BromomethylstyreneHCID 5462224Magnesium

Product 1

HCID 400031'-Hydroxyestragole

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Instead of the cinnamyl bromide, the chloride may also be used. Illustrative of its preparation is the following procedure: To the Grignard reagent, prepared from 2.25 g of magnesium, 9.75 g of vinyl bromide and 50 ml of tetrahydrofuran, the solution of 10.2 g of 4-methoxybenzaldehyde in 75 ml of diethyl ether is added dropwise while stirring under nitrogen and cooling with ice. The mixture is stirred for 2 hours at room temperature, again cooled, and 12 ml of saturated aqueous ammonium chloride are added dropwise. The resulting suspension is filtered, the filtrate dried and evaporated, to yield the 4-methoxy-α-vinylbenzyl alcohol.

Workup

  1. customIllustrative of its preparation
  2. temperaturecooling with ice
  3. stirringThe mixture is stirred for 2 hours at room temperature
  4. temperatureagain cooled
  5. filtrationThe resulting suspension is filtered
  6. customthe filtrate dried
  7. customevaporated

Sources & evidence

ORD record
ord-07fb80cf04d64d968e774fae2e533386
Source dataset
uspto-grants-1976_08
Patent number
US03973030

Reaction notes

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