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

HRID 1679616Notes

Reaction equation

HRID 1679616 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-e18bc71998564db181d38f56bd67014a
Source dataset
uspto-grants-1978_03
Patent number
US04081476

Reaction notes

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