Hydrochloric Acid → (4-Chlorophenyl)(4-cyanophenyl)methanol

HRID 1663594Notes

Reaction equation

HRID 1663594 reaction equation
[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[CH:5][CH:4]=1)#[N:2].[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([Mg]Br)=[CH:14][CH:13]=1.C(OCC)C.Cl>C(=O)=O.CO>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([CH:7]([C:6]2[CH:9]=[CH:10][C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)[OH:8])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 660424-CyanobenzaldehydeHCID 178467826HCID 178467826, compound

Product 1

HCID 67001080(4-Chlorophenyl)(4-cyanophenyl)methanolYield 96%

Reagents, catalysts & solvents 1

HCID 21973728Carbon dioxide methanolSolvent

Procedure

To a solution of 4-cyanobenzaldehyde (3.93 g) in tetrahydrofaran was added dropwise 1.0M 4-chlorophenylmagnesium bromide-diethylether (30 mL) under nitrogen gas atmosphere and cooling in dry ice/methanol bath and the mixture was stirred at the same temperature for 10 minutes. To the reaction mixture was added 10% HCl solution and the aqueous layer was extracted with ethyl acetate (×2). The organic layer was washed with a saturated brine, dried over magnesium sulfate and concentrated in vacuo. To the resultant crude product was added diisopropyl ether and the resultant solid materials were collected by filtration to give (4-chlorophenyl)(4-cyanophenyl)methanol (6.98 g, yield: 96%) as a pale yellow solid.

Workup

  1. extractionthe aqueous layer was extracted with ethyl acetate (×2)
  2. washThe organic layer was washed with a saturated brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. additionTo the resultant crude product was added diisopropyl ether
  6. filtrationthe resultant solid materials were collected by filtration

Sources & evidence

ORD record
ord-79a58ad7274a4720b057ffb930410173
Source dataset
uspto-grants-2011_10
Patent number
US08034949B2

Reaction notes

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