Hydrochloric Acid → 1-(4-Benzyloxy-3-chlorophenyl)-2,2,2-trifluoroethanol

HRID 2113161

Reaction equation

HRID 2113161 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][C:10]=1[Cl:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si](C)(C)[C:20]([F:23])([F:22])[F:21].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.Cl>C1COCC1.C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]([OH:14])[C:20]([F:23])([F:22])[F:21])=[CH:11][C:10]=1[Cl:17])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 27354954-(Benzyloxy)-3-chlorobenzaldehyde

Product 1

HCID 690509761-(4-Benzyloxy-3-chlorophenyl)-2,2,2-trifluoroethanol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 4-benzyloxy-3-chlorobenzaldehyde (4.9 g, 20 mmol) and trimethyl(trifluoromethyl)silane (4.4 mL, 30 mmol) in THF (0.10 L) was added a solution tetrabutylammonium fluoride (1.0 M in THF, 2.0 mL). After the reaction was stirred at 25° C. for 3 h, it was acidified with 2 N HCl to pH 2, diluted with ethyl acetate and washed with brine. The organic phase was dried and concentrated and the residue was purified by chramotography on silica gel eluting with 8:2 hexane:ethyl acetate to give 1-(4-benzyloxy-3-chlorophenyl)-2,2,2-trifluoroethanol.

Workup

  1. washwashed with brine
  2. customThe organic phase was dried
  3. concentrationconcentrated
  4. customthe residue was purified by chramotography on silica gel eluting with 8:2 hexane

Sources & evidence

ORD record
ord-b99b7676da0141c19ba218f3fcf51726
Source dataset
uspto-grants-2009_04
Patent number
US07524882B2

Linked notes

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