Tetrahydrofuran → 2-(p-Biphenylyl)-2-penten-4-ol

HRID 67134Notes

Reaction equation

HRID 67134 reaction equation
[C:1]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7](=[CH:9][C:10](=[O:12])[CH3:11])[CH3:8].O1CCCC1.CC[Al-]CC.[Na+]>C1(C)C=CC=CC=1>[C:1]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7](=[CH:9][CH:10]([OH:12])[CH3:11])[CH3:8]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 16687524Sodium aluminum diethyl dihydrideHCID 545652342-(p-Biphenylyl)-2-penten-4-one

Product 1

HCID 705454192-(p-Biphenylyl)-2-penten-4-ol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 1.6 g. 2-(p-biphenylyl)-2-penten-4-one in 25 ml. of dry tetrahydrofuran, at 0° C., 10 ml. of a solution of 25% (W/W) of sodium aluminum diethyl dihydride in toluene is dropwise added. After 20 minutes at 0° C., the mixture is poured onto ice and extracted with chloroform. Evaporation of the chloroform gives 2-(p-biphenylyl)-2-penten-4-ol, m.p. 137°-138° C.

Workup

  1. customat 0° C.
  2. additionthe mixture is poured onto ice
  3. extractionextracted with chloroform
  4. customEvaporation of the chloroform

Sources & evidence

ORD record
ord-b2819e8526c1468bac09f8e4a79d25da
Source dataset
uspto-grants-1982_08
Patent number
US04344966

Reaction notes

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