Hydrochloric Acid → 3-Isopropoxy-4-nitrobenzoic acid

HRID 278839

Reaction equation

HRID 278839 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([O-:10])=[O:9])=[C:6](CC)[C:5]=1[O:15][CH:16]([CH3:18])[CH3:17])([O-:3])=[O:2].[OH-].[K+].Cl>C(O)C.O>[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][C:5]=1[O:15][CH:16]([CH3:18])[CH3:17])([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 178301674-Nitro-3-isopropoxy-ethylbenzoate

Product 1

HCID 6029283-Isopropoxy-4-nitrobenzoic acidYield 88.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

To a solution of 4-nitro-3-isopropoxy-ethylbenzoate (11.85 g, 0.047 mol) in ethanol (200 mL) was added a solution of potassium hydroxide (2.6 g, 0.047 mol) in water (5 mL). The reaction mixture was heated to reflux for 2 hours. The ethanol volume was reduced to 100 mL and the mixture then poured into 1 N HCl (100 mL). The crystals that precipitated, were filtered off and dried in a vacuum oven to yield 9.35 g (88%) of 4-nitro-3-isopropoxybenzoic acid. MS ES− 225, ES+ 223.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 2 hours
  3. customThe crystals that precipitated
  4. filtrationwere filtered off
  5. customdried in a vacuum oven

Sources & evidence

ORD record
ord-8af2072f27904393ab9fccf4bbb71581
Source dataset
uspto-grants-2002_03
Patent number
US06361931B1

Linked notes

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