Trichloroacetonitrile → p-Chloro-alpha,alpha-dimethylbenzyl alcohol

HRID 1367597Notes

Reaction equation

HRID 1367597 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([OH:13])([CH3:12])[CH3:11])=[CH:6][CH:5]=1.[Cl:14][C:15]([Cl:19])([Cl:18])[C:16]#[N:17]>CCOCC>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]([O:13][C:16](=[NH:17])[C:15]([Cl:19])([Cl:18])[Cl:14])([CH3:11])[CH3:12])=[CH:8][CH:9]=1.[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]([OH:13])([CH3:11])[CH3:12])=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 11011TrichloroacetonitrileHCID 24758Sodium hydrideHCID 74808p-Chloro-alpha,alpha-dimethylbenzyl alcohol

Product 2

HCID 74808p-Chloro-alpha,alpha-dimethylbenzyl alcoholHCID 66918649HCID 66918649, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a suspension of sodium hydride (5.63 mg, 0.117 mmol) in ether was added a solution of 2-(4-chloro-phenyl)-propan-2-ol (CAS 1989-25-9) in ether (1.5 ml) at 0° C. The mixture was stirred for 90 minutes, then trichloroacetonitrile (112 μl, 1.11 mmol) was added and stirring was continued for 3 h at 0° C. Then all volatiles were removed and pentane (1 ml) and MeOH (4.74 μl) were added. The suspension was stirred for 1 h. Filtration and concentration of the filtrate yielded the title compound in a mixture with 2-(4-chloro-phenyl)-propan-2-ol which was used in the next reaction step without further purification.

Workup

  1. stirringstirring
  2. waitwas continued for 3 h at 0° C
  3. customThen all volatiles were removed
  4. additionpentane (1 ml) and MeOH (4.74 μl) were added
  5. stirringThe suspension was stirred for 1 h
  6. filtrationFiltration and concentration of the filtrate

Sources & evidence

ORD record
ord-cd42fc80f07449b2ba6e827e833976b4
Source dataset
uspto-grants-2011_02
Patent number
US07893099B2

Reaction notes

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