Dimethylformamide → HCID 23055432, compound

HRID 2108084Notes

Reaction equation

HRID 2108084 reaction equation
[N+:1]([C:4]1[C:5]([OH:14])=[C:6]([O:12][CH3:13])[CH:7]=[C:8]([CH:11]=1)[CH:9]=[O:10])([O-:3])=[O:2].[CH2:15](Cl)[CH2:16][CH2:17][CH3:18].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH2:15]([O:14][C:5]1[C:4]([N+:1]([O-:3])=[O:2])=[CH:11][C:8]([CH:9]=[O:10])=[CH:7][C:6]=1[O:12][CH3:13])[CH2:16][CH2:17][CH3:18]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8005Butyl ChlorideHCID 11430Potassium CarbonateHCID 811345-Nitrovanillin

Product 1

HCID 23055432HCID 23055432, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5-nitrovanillin (2.2 g), butyl chloride (10 ml), potassium carbonate (8 g) and N,N-dimethylformamide (50 ml) is stirred at 100° C. for 24 hours. After cooling, water (300 ml) is added to the reaction mixture, followed by extraction with ethyl acetate (200 ml). The extract solution is washed with water, dried, and concentrated under reduced pressure. The residue is purified by means of a silica gel column chromatography (hexane: ethyl acetate=1:1) to afford 4-butoxy-3-methoxy-5-nitrobenzaldehye (2 g) as a pale yellow oily product. This product is dissolved in acetone (100 ml), potassium permanganate (6 g) is added to the mixture, and the mixture is stirred at room temperature overnight. To the reaction mixture are added ethanol (20 ml), water (20 ml) and acetone (200 ml). The whole mixture is left standing for two hours, then insolubles are filtered off. The filtrate is concentrated under reduced pressure. The concentrate is dissolved in water (100 ml) and the mixture is acidified with concentrated hydrochloric acid. Precipitating crystals are collected by filtration to afford 4-butoxy-3-methoxy-5-nitrobenzoic acid (1.6 g) as colorless crystals. This product is recrystallized from a mixture of ethanol and water to give colorless prisms, m.p. 114°-115° C.

Workup

  1. temperatureAfter cooling
  2. extractionfollowed by extraction with ethyl acetate (200 ml)
  3. washThe extract solution is washed with water
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by means of a silica gel column chromatography (hexane: ethyl acetate=1:1)

Sources & evidence

ORD record
ord-c6cda8cfaec84a20b63ef810365c008d
Source dataset
uspto-grants-1990_06
Patent number
US04937246

Reaction notes

Loading…