3-Hydroxybenzyl alcohol → (3-(4-(Trifluoromethyl)phenoxy)phenyl)methanol

HRID 1666422Notes

Reaction equation

HRID 1666422 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.F[C:11]1[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O>[F:18][C:17]([F:20])([F:19])[C:14]1[CH:15]=[CH:16][C:11]([O:9][C:5]2[CH:4]=[C:3]([CH2:2][OH:1])[CH:8]=[CH:7][CH:6]=2)=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 1023-Hydroxybenzyl alcoholHCID 10796Cesium carbonateHCID 67873Benzene, 1-fluoro-4-(trifluoromethyl)-

Product 1

HCID 23136407(3-(4-(Trifluoromethyl)phenoxy)phenyl)methanolYield 60.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
110 °C

Procedure

3-Hydroxymethyl-phenol (1.0 g, 8.1 mmol), 4-fluorobenzotrifluoride (1.32 g, 8.1 mmol) and cesium carbonate (3.28 g, 10.1 mmol) were suspended in dimethylsulfoxide (15 mL) and heated to 110° C. After stirring for 16 h, the reaction was partitioned between water (150 mL) and ethyl acetate (150 mL). The organic layer was separated and the aqueous was extracted again with ethyl acetate. The combined organic layer was dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography (10-40%, EtOAc:heptane) to afford the title compound (1.32 g) as a thick oil.

Workup

  1. customthe reaction was partitioned between water (150 mL) and ethyl acetate (150 mL)
  2. customThe organic layer was separated
  3. extractionthe aqueous was extracted again with ethyl acetate
  4. dry with materialThe combined organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography (10-40%, EtOAc:heptane)

Sources & evidence

ORD record
ord-8b018529f8d64f4faf6f6d7669e52933
Source dataset
uspto-grants-2011_10
Patent number
US08044052B2

Reaction notes

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