Formaldehyde → Methyl 4-(1-diphenylmethoxycarbonyl-2-hydroxyethyl)-2,3,5,6-tetrafluorobenzoate

HRID 981260Notes

Reaction equation

HRID 981260 reaction equation
[C:1]1([CH:7]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[O:8][C:9]([CH2:11][C:12]2[C:21]([F:22])=[C:20]([F:23])[C:15]([C:16]([O:18][CH3:19])=[O:17])=[C:14]([F:24])[C:13]=2[F:25])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C=O.[C:34](OCC)(=[O:36])C.O>CN(C)C=O.C[O-].[Na+]>[C:26]1([CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[O:8][C:9]([CH:11]([C:12]2[C:13]([F:25])=[C:14]([F:24])[C:15]([C:16]([O:18][CH3:19])=[O:17])=[C:20]([F:23])[C:21]=2[F:22])[CH2:34][OH:36])=[O:10])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 962WaterHCID 8857Ethyl AcetateHCID 15136246Methyl 4-diphenylmethoxycarbonylmethyl-2,3,5,6tetrafluorobenzoate

Product 1

HCID 15136247Methyl 4-(1-diphenylmethoxycarbonyl-2-hydroxyethyl)-2,3,5,6-tetrafluorobenzoateYield 67%

Reagents, catalysts & solvents 2

HCID 10942334Sodium MethoxideCatalystHCID 6228DimethylformamideSolvent

Procedure

In 486 ml of N,N-dimethylformamide was dissolved 8.6 g of methyl 4-diphenylmethoxycarbonylmethyl-2,3,5,6tetrafluorobenzoate. To the resulting solution were added 3.54 g of paraformaldehyde and 61 mg of sodium methylate in this order. The resulting mixture was stirred at room temperature for 2 hours. To the reaction mixture were added 300 ml of ethyl acetate and 800 ml of water in this order. The organic layer was separated, washed with water and a saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue obtained was purified by a column chromatography (eluant: toluene/ethyl acetate=10/1) to obtain 35.0 g (yield: 67.0%) of methyl 4-(1-diphenylmethoxycarbonyl-2-hydroxyethyl)-2,3,5,6-tetrafluorobenzoate.

Workup

  1. customThe organic layer was separated
  2. washwashed with water
  3. dry with materiala saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate
  4. customThe solvent was removed by distillation under reduced pressure
  5. customThe residue obtained
  6. customwas purified by a column chromatography (eluant: toluene/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-06217ae6be1b419585d3e9f8d0d05ecf
Source dataset
uspto-grants-1991_02
Patent number
US04990508

Reaction notes

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