Hydrochloric Acid → 3-Hydroxy-3,3-diphenylpropanenitrile

HRID 596158Notes

Reaction equation

HRID 596158 reaction equation
[C:1](#[N:3])[CH3:2].C([Li])CCC.[C:9]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.Cl>O1CCCC1.CCCCCC>[OH:16][C:9]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:2][C:1]#[N:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3102BenzophenoneHCID 6342AcetonitrileHCID 178418339Butyllithium

Product 1

HCID 2660763-Hydroxy-3,3-diphenylpropanenitrile

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8058HexaneSolvent

Procedure

The solution of 8.2 g of acetonitrile in 200 ml of tetrahydrofuran is added dropwise to the solution of 14.08 g of butyl lithium in 125 ml of tetrahydrofuran and 125 ml of n-hexane while stirring at -70° under nitrogen and stirring is continued for 1 hour. Thereupon the solution of 36.4 g benzophenone in 200 ml of tetrahydrofuran is added dropwise and the mixture stirred for 20 minutes at room temperature. It is poured onto 300 g of ice and 100 ml of 3N hydrochloric acid, the organic layer separated and the aqueous phase extracted three times with 50 ml of diethyl ether. The combined organic solutions are dried, evaporated and the residue recrystallized from ethanol, to yield the β-hydroxy-β,β-diphenyl-propionitrile melting at 136°-138°.

Workup

  1. stirringstirring
  2. stirringthe mixture stirred for 20 minutes at room temperature
  3. customthe organic layer separated
  4. extractionthe aqueous phase extracted three times with 50 ml of diethyl ether
  5. customThe combined organic solutions are dried
  6. customevaporated
  7. customthe residue recrystallized from ethanol

Sources & evidence

ORD record
ord-2a995907b73c40e993b011319e73a8c6
Source dataset
uspto-grants-1977_03
Patent number
US04010166

Reaction notes

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