Diethyl Ether → HCID 20324255, compound

HRID 441351Notes

Reaction equation

HRID 441351 reaction equation
[OH:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[CH3:16][CH2:17]OCC.C([Mg]Cl)=C.[Cl-].[NH4+]>O1CCCC1>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([CH:16]=[CH2:17])([OH:7])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 143474-HydroxybenzophenoneHCID 25517Ammonium ChlorideHCID 178461836HCID 178461836, compound

Product 1

HCID 20324255HCID 20324255, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 20 g. of 4-hydroxy-benzophenone in 180 ml. of dry ether is added, within about 30 minutes, to a 0° C. solution of 184 ml. of a 3.4 molar tetrahydrofuran solution of vinyl magnesium chloride, and the reaction mixture is stirred at the same temperature for additional 1 hour. The mixture is allowed to stand at room temperature overnight. Thereafter the mixture is poured onto ice water containing ammonium chloride. The etheral phase is separated, washed with water until neutral, dried over anhydrous mganesium sulfate, and the solvent is evaporated. 22.6 g. of crude 4-hydroxy-α-vinyl-benzhydrol are obtained. After recrystallization from a mixture of ethyl acetate and n-hexane, the product melts at 104°-105° C.

Workup

  1. additionThereafter the mixture is poured onto ice water
  2. customThe etheral phase is separated
  3. washwashed with water until neutral,
  4. dry with materialdried over anhydrous mganesium sulfate
  5. customthe solvent is evaporated

Sources & evidence

ORD record
ord-84f5782096294e8887f02700b290a113
Source dataset
uspto-grants-1977_08
Patent number
US04039589

Reaction notes

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