Water → Isopropyl 4-chloro-3-nitrobenzoate

HRID 2399721Notes

Reaction equation

HRID 2399721 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].C(N(CC)CC)C.[CH:21]([OH:24])([CH3:23])[CH3:22].O>C(OCC)(=O)C>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:24][CH:21]([CH3:23])[CH3:22])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12]

Participants

6

Reactant 4

HCID 962WaterHCID 3776IsopropanolHCID 8471TriethylamineHCID 1234774-Chloro-3-nitrobenzoyl chloride

Product 1

HCID 693119Isopropyl 4-chloro-3-nitrobenzoateYield 99.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a stirred solution of 4-chloro-3-nitrobenzoyl chloride (20.5 g) in ethyl acetate (80 cm3) was added a solution of triethylamine (10.1 g) and i-propylalcohol (6 g) in ethylacetate (40 cm3) over 15 mins causing a slight exotherm. The reaction was stirred at the ambient temperature for a further 3.5 hours and then poured into water. The layers were separated and the aqueous layer was extracted with ethyl acetate and the combined ethyl acetate layers were washed with 10% HCl, brine and dried with sodium sulphate. Filtration and evaporation gave iso-propyl 4-chloro-3-nitrobenzoate as a yellow solid (22.5 g). 1H nmr (CDCl3) d: 8.49 (1H, d), 8.17 (1H, dd), 7.64 (1H, d), 5.29 (1H, septet), 1.40 (6H, d). Mpt 61°-62° C.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. washthe combined ethyl acetate layers were washed with 10% HCl, brine
  4. dry with materialdried with sodium sulphate
  5. filtrationFiltration and evaporation

Sources & evidence

ORD record
ord-d6d7c051385a47d38cee0e56807b920d
Source dataset
uspto-grants-1995_09
Patent number
US05451594

Reaction notes

Loading…