Pyridine → 3,5-Dinitrobenzoic acid 6-[2-methoxy-4-(2-methoxycarbonylvinyl)phenoxy]hexyl ester

HRID 1250801Notes

Reaction equation

HRID 1250801 reaction equation
[CH3:1][O:2][C:3](=[O:22])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][OH:19])=[C:8]([O:20][CH3:21])[CH:7]=1.[N+:23]([C:26]1[CH:27]=[C:28]([CH:32]=[C:33]([N+:35]([O-:37])=[O:36])[CH:34]=1)[C:29](Cl)=[O:30])([O-:25])=[O:24].N1C=CC=CC=1>C(Cl)Cl.CN(C1C=CC=CN=1)C>[C:3]([O-:22])(=[O:2])[CH3:4].[CH3:21][O:20][C:8]1[CH:7]=[C:6]([CH:5]=[CH:4][C:3]([O:2][CH3:1])=[O:22])[CH:11]=[CH:10][C:9]=1[O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:19][C:29](=[O:30])[C:28]1[CH:27]=[C:26]([N+:23]([O-:25])=[O:24])[CH:34]=[C:33]([N+:35]([O-:37])=[O:36])[CH:32]=1

Participants

7

Reactant 3

HCID 1049PyridineHCID 74323,5-Dinitrobenzoyl chlorideHCID 541470624-(6-Hydroxyhexyloxy)-3-methoxycinnamic acid methyl ester

Product 2

HCID 175AcetateHCID 543196263,5-Dinitrobenzoic acid 6-[2-methoxy-4-(2-methoxycarbonylvinyl)phenoxy]hexyl esterYield 176.7%

Reagents, catalysts & solvents 2

HCID 218852-DimethylaminopyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

2.50 g (8.11 mmol) of 4-(6-hydroxyhexyloxy)-3-methoxycinnamic acid methyl ester, 1.96 g (8.51 mmol) of 3,5-dinitrobenzoyl chloride and 10 mg (0.08 mmol) of dimethylaminopyridine were dissolved in 25 ml of methylene chloride. 3.3 ml (40.5 mmol) of pyridine were added dropwise, in the course of 20 minutes at 0° C., to the resulting clear solution. After 2 hours at 0° C. the reaction mixture was partitioned between methylene chloride and water; the organic phase was washed with a saturated sodium bicarbonate solution and repeatedly with water. The organic phase was then dried over magnesium sulphate, filtered and concentrated by evaporation. Chromatography of the residue on 150 g of silica gel using toluenelethyl acetate 9:1 yielded 3.6 g of 3,5-dinitrobenzoic acid 6-[2-methoxy-4-(2-methoxycarbonylvinyl)phenoxy]hexyl ester.

Workup

  1. customAfter 2 hours at 0° C. the reaction mixture was partitioned between methylene chloride and water
  2. washthe organic phase was washed with a saturated sodium bicarbonate solution and repeatedly with water
  3. dry with materialThe organic phase was then dried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-e338315390d74529a9fdeb31a01793ea
Source dataset
uspto-grants-2002_01
Patent number
US06340506B1

Reaction notes

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