Sodium hydride → Methyl 2-(4-trifluoromethylbenzyloxy)-3-methylbenzoate

HRID 1814788Notes

Reaction equation

HRID 1814788 reaction equation
[H-].[Na+].[OH:3][C:4]1[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7].[F:15][C:16]([F:26])([F:25])[C:17]1[CH:24]=[CH:23][C:20]([CH2:21]Br)=[CH:19][CH:18]=1>CN(C=O)C>[F:15][C:16]([F:25])([F:26])[C:17]1[CH:24]=[CH:23][C:20]([CH2:21][O:3][C:4]2[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][C:5]=2[C:6]([O:8][CH3:9])=[O:7])=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 31835Benzoic acid, 2-hydroxy-3-methyl-, methyl esterHCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzene

Product 1

HCID 22498800Methyl 2-(4-trifluoromethylbenzyloxy)-3-methylbenzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride is added to a solution of methyl 2-hydroxy-3-methylbenzoate (694 mg, 4.18 mmol) in 15 mL of DMF at 0° C. The reaction is stirred for 15 minutes after which 4-trifluoromethyl-benzyl bromide (1.0 g, 4.18 mmol) is added. The reaction is allowed to warm up to room temperature and stirred overnight. The mixture is partitioned between ethyl acetate and water. The organic phase is washed with brine, dried over sodium sulfate, filtered and concentrated. The residue is chromatographed on silica gel using 4% ethyl acetate in hexane as the eluent to obtain methyl 2-(4-trifluoromethylbenzyloxy)-3-methylbenzoate as a clear liquid.

Workup

  1. additionis added
  2. customThe mixture is partitioned between ethyl acetate and water
  3. washThe organic phase is washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue is chromatographed on silica gel using 4% ethyl acetate in hexane as the eluent

Sources & evidence

ORD record
ord-c3724a4285024340a46604fc3d970b90
Source dataset
uspto-grants-2005_04
Patent number
US06878707B2

Reaction notes

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