Ethyl orthoformate → HCID 58279341, compound

HRID 85107Notes

Reaction equation

HRID 85107 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5](C=O)=[C:4]([C:10]([F:13])([F:12])[F:11])[CH:3]=1.C(O[CH:17]([O:21][CH2:22]C)[O:18][CH2:19]C)C.CO[Na]>CO>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:17]([O:18][CH3:19])[O:21][CH3:22])=[C:4]([C:10]([F:11])([F:12])[F:13])[CH:3]=1

Participants

5

Reactant 3

HCID 31214Ethyl orthoformateHCID 27790174-Chloro-2-(trifluoromethyl)benzaldehydeHCID 178418582HCID 178418582, compound

Product 1

HCID 58279341HCID 58279341, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a stirred solution of 4-chloro-2-(trifluoromethyl)benzaldehyde (17; 4.20 g, 20.0 mmol) in methanol (25 mL) was added triethoxymethane (3.60 g, 24.0 mmol) at 0° C. The resulting reaction mixture was warmed to room temperature and stirred for 12 h. A solution of MeONa in methanol was added to adjust the pH=10. The solvent was removed under reduced pressure and the resulting residue was diluted with water. The mixture was extracted with ethyl acetate (3×50 mL) and the combined organic layers were dried (Na2SO4) and concentrated under reduced pressure to give 4-chloro-1-(dimethoxymethyl)-2-(trifluoromethyl)benzene 18 (3.20 g, 12.6 mmol, 63%).

Workup

  1. customThe resulting reaction mixture
  2. customThe solvent was removed under reduced pressure
  3. additionthe resulting residue was diluted with water
  4. extractionThe mixture was extracted with ethyl acetate (3×50 mL)
  5. dry with materialthe combined organic layers were dried (Na2SO4)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-adbb60753d72486985e8ec44240215e0
Source dataset
uspto-grants-2014_09
Patent number
US08846947B2

Reaction notes

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