Water → Methyl (4'-{[2-formyl-3-hydroxy-4-(trifluoromethyl)benzyl]oxy}-1,1'-biphenyl-3-yl)acetate

HRID 2076594Notes

Reaction equation

HRID 2076594 reaction equation
O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C[O:14][CH:15](OC)[C:16]1[C:40]([O:41]COC)=[C:39]([C:45]([F:48])([F:47])[F:46])[CH:38]=[CH:37][C:17]=1[CH2:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([CH2:32][C:33]([O:35][CH3:36])=[O:34])[CH:27]=2)=[CH:22][CH:21]=1.O>CC(C)=O>[CH:15]([C:16]1[C:40]([OH:41])=[C:39]([C:45]([F:46])([F:48])[F:47])[CH:38]=[CH:37][C:17]=1[CH2:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([CH2:32][C:33]([O:35][CH3:36])=[O:34])[CH:27]=2)=[CH:22][CH:21]=1)=[O:14]

Participants

5

Reactant 3

HCID 962WaterHCID 521998p-Toluenesulfonic acid monohydrateHCID 86617397Methyl (4'-{[2-(dimethoxymethyl)-3-(methoxymethoxy)-4-(trifluoromethyl)benzyl]oxy}-1,1'-biphenyl-3-yl)acetate

Product 1

HCID 86617398Methyl (4'-{[2-formyl-3-hydroxy-4-(trifluoromethyl)benzyl]oxy}-1,1'-biphenyl-3-yl)acetateYield 83%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

After p-toluenesulfonic acid monohydrate (0.716 g, 3.77 mmol) was added to a solution of methyl (4′-{[2-(dimethoxymethyl)-3-(methoxymethoxy)-4-(trifluoromethyl)benzyl]oxy}-1,1′-biphenyl-3-yl)acetate (1.83 g, 3.43 mmol) obtained in Example (8-2) in acetone (20 ml), the mixture was stirred at room temperature for 6 hours. After the reaction mixture was poured into water and the mixture was extracted with ethyl acetate (twice), the organic layer was successively washed with water and a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate. The solvent was removed under reduced pressure to give a residue. The obtained residue was purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=80/20-70/30) to give methyl (4′-{[2-formyl-3-hydroxy-4-(trifluoromethyl)benzyl]oxy}-1,1′-biphenyl-3-yl)acetate (1.26 g, yield: 83%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate (twice), the organic layer
  2. washwas successively washed with water
  3. dry with materiala saturated aqueous NaCl solution and dried with anhydrous sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customto give a residue
  6. customThe obtained residue was purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=80/20-70/30)

Sources & evidence

ORD record
ord-b047a8c370454146a23a61acf3753d9d
Source dataset
uspto-grants-2011_04
Patent number
US07923573B2

Reaction notes

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