1-Methoxy-2-propanol → HCID 53729442, compound

HRID 1165264Notes

Reaction equation

HRID 1165264 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7])([O-:3])=[O:2].[CH3:16][O:17][CH2:18][CH:19](O)[CH3:20]>C1(C)C=CC=CC=1.C1(C)C(S(O)(=O)=O)=CC=CC=1>[CH3:16][O:17][CH2:18][CH:19]([O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:11]([N+:13]([O-:15])=[O:14])=[CH:12][C:4]=1[N+:1]([O-:3])=[O:2])[CH3:20]

Participants

5

Reactant 2

HCID 79001-Methoxy-2-propanolHCID 118802,4-Dinitrobenzoic acid

Product 1

HCID 53729442HCID 53729442, compoundYield 53.5%

Reagents, catalysts & solvents 2

HCID 69252-Methylbenzenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

To a mixture of 212.0 g of 2,4-dinitrobenzoic acid in 300 ml of toluene were added 4.0 g of toluenesulfonic acid and 180.2 g of 1-methoxy-2-propanol. The mixture was refluxed for 48 hrs and the resulting water removed by azeotropic distillation. After this period the mixture was cooled to room temperture and washed with 500 ml of an aqueous 5% NaHCO3 solution followed by two 150 ml water washings. The toluene was removed at reduced pressure and the resulting oil was washed with hexane to give 152 g (1-methoxy-2-propyl)-2,4-dinitrobenzoate, a tan solid, mp 42° C.

Workup

  1. temperatureThe mixture was refluxed for 48 hrs
  2. customthe resulting water removed by azeotropic distillation
  3. temperatureAfter this period the mixture was cooled to room temperture
  4. washwashed with 500 ml of an aqueous 5% NaHCO3 solution
  5. customThe toluene was removed at reduced pressure
  6. washthe resulting oil was washed with hexane

Sources & evidence

ORD record
ord-f39adf88a349473a9b46110ed4f35c81
Source dataset
uspto-grants-1990_03
Patent number
US04908394

Reaction notes

Loading…