Hydrochloric Acid → 4-Trifluoromethyl-alpha,alpha-dimethylbenzyl chloride

HRID 726138Notes

Reaction equation

HRID 726138 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:12]=[CH:11][C:6]([C:7](O)([CH3:9])[CH3:8])=[CH:5][CH:4]=1.[ClH:15]>[Cl-].[Zn+2].[Cl-]>[F:1][C:2]([F:14])([F:13])[C:3]1[CH:12]=[CH:11][C:6]([C:7]([Cl:15])([CH3:9])[CH3:8])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 27776172-(4-(Trifluoromethyl)phenyl)-2-propanol

Product 1

HCID 197097954-Trifluoromethyl-alpha,alpha-dimethylbenzyl chloride

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

The alcohol from step A above (54 g, 0.27 mol) is treated with ethereal HCl (1.3 L, 1M) followed by anhydrous zinc chloride (53 mL, 1M in ether) and the reaction allowed to stir for 22 h at room temperature. The reaction is then washed with water, aqueous 2 N NaOH, dried over MgSO4, concentrated and purified by silica gel chromatography (8:1 hexane to ethyl acetate) to give 4-trifluoromethyl-α,α-dimethylbenzyl chloride of sufficient purity to carry to the next step; yield: 50.5 g (85%).

Workup

  1. washThe reaction is then washed with water, aqueous 2 N NaOH
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. custompurified by silica gel chromatography (8:1 hexane to ethyl acetate)

Sources & evidence

ORD record
ord-660483652906462181666f120083ce9b
Source dataset
uspto-grants-1998_01
Patent number
US05708001

Reaction notes

Loading…