Trimethyl orthoformate → 1-Dimethoxymethyl-5-fluoro-2-methoxy-4-nitro-benzene

HRID 1667784Notes

Reaction equation

HRID 1667784 reaction equation
[F:1][C:2]1[C:3]([N+:12]([O-:14])=[O:13])=[CH:4][C:5]([O:10][CH3:11])=[C:6]([CH:9]=1)C=O.CO[CH:17]([O:20][CH3:21])[O:18][CH3:19].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>CO>[CH3:21][O:20][CH:17]([O:18][CH3:19])[C:6]1[CH:9]=[C:2]([F:1])[C:3]([N+:12]([O-:14])=[O:13])=[CH:4][C:5]=1[O:10][CH3:11]

Participants

6

Reactant 4

HCID 9005Trimethyl orthoformateHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 862228455-Fluoro-2-methoxy-4-nitrobenzaldehyde

Product 1

HCID 674266731-Dimethoxymethyl-5-fluoro-2-methoxy-4-nitro-benzene

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 0.210 g (1.06 mmole) of 5-fluoro-2-methoxy-4-nitro-benzaldehyde (IV.46c), 1 mL of trimethylorthoformate, 0.025 g of p-toluenesulfonic acid monohydrate and 5 mL of methanol was heated at reflux for one hour. The mixture was cooled, neutralized by addition of saturated sodium bicarbonate solution and concentrated under reduced pressure. The residue was partitioned between ethyl acetate and saturated sodium bicarbonate solution. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give 0.243 g of 1-dimethoxymethyl-5-fluoro-2-methoxy-4-nitro-benzene (IV.46d) as a yellow oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for one hour
  3. temperatureThe mixture was cooled
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was partitioned between ethyl acetate and saturated sodium bicarbonate solution
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7c1f0805e1364af38007b03c0827af1c
Source dataset
uspto-grants-2011_10
Patent number
US08044213B2

Reaction notes

Loading…