Isopropanol → HCID 19363214, compound

HRID 850469Notes

Reaction equation

HRID 850469 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[C:5]([N+:11]([O-:13])=[O:12])[C:4]=1[O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].S(N)(=O)(=O)[OH:21].C(O)(C)C.Cl([O-])=O.[Na+]>C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]([OH:21])=[O:8])=[C:5]([N+:11]([O-:13])=[O:12])[C:4]=1[O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 5987Sulfamic AcidHCID 11608682HCID 11608682, compoundHCID 23668197Sodium Chlorite

Product 1

HCID 19363214HCID 19363214, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-Methoxy-2-nitro-3-pentyloxybenzaldehyde (70 g, 261.9 mmol), amidosulfuric acid (76.3 g, 785.7 mmol) and isopropanol (210 ml) were mixed, an aqueous sodium chlorite (38.5 g, 340.5 mmol) solution (350 ml) was added dropwise to this solution while cooling in a water bath. After stirring for 20 minutes, ethyl acetate (300 ml) was added to separate the organic layer. The aqueous layer was extracted with ethyl acetate (200 ml). The organic layers were combined, washed with saturated brine (150 ml), and dried over anhydrous magnesium sulfate. The drying agent was filtered off and the filtrate was concentrated under reduced pressure. The precipitated crystals were collected by filtration to give 4-methoxy-2-nitro-3-pentyloxybenzoic acid (59.02 g, 80%) as pale-yellow crystals.

Workup

  1. temperaturewhile cooling in a water bath
  2. customto separate the organic layer
  3. extractionThe aqueous layer was extracted with ethyl acetate (200 ml)
  4. washwashed with saturated brine (150 ml)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationThe drying agent was filtered off
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. filtrationThe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-f21b9cc92ea24ba58e097c5b86c92799
Source dataset
uspto-grants-2000_01
Patent number
US06017919

Reaction notes

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