Hydrochloric Acid → HCID 17989410, compound

HRID 1353074Notes

Reaction equation

HRID 1353074 reaction equation
C([O:4][C:5](=[O:19])[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH:14]=[CH2:15])=[CH:8][C:7]=1[N+:16]([O-:18])=[O:17])C=C.[OH-].[Na+].Cl>C(O)C>[CH2:13]([O:12][C:9]1[CH:10]=[CH:11][C:6]([C:5]([OH:19])=[O:4])=[C:7]([N+:16]([O-:18])=[O:17])[CH:8]=1)[CH:14]=[CH2:15]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 69422172HCID 69422172, compound

Product 1

HCID 17989410HCID 17989410, compoundYield 89.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-allyloxy-2-nitro-benzoic acid allyl ester [J. Org. Chem. 1987, 52(18), 4086] (0.21 g, 0.8 mmol) was dissolved in ethanol (5 ml), and 40% sodium hydroxide added (5 ml). The mixture was stirred for 16 h then acidified to pH 2 with 2M hydrochloric acid. The mixture was extracted with ethyl acetate (3×25 ml) and the combined organic phases washed with brine (75 ml), dried (MgSO4) and concentrated to yield 4-allyloxy-2-nitrobenzoic acid as brown solid (0.16 g);

Workup

  1. extractionThe mixture was extracted with ethyl acetate (3×25 ml)
  2. washthe combined organic phases washed with brine (75 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3fbb65f752724479ae0bf5d1473934ec
Source dataset
uspto-grants-2007_05
Patent number
US07220777B2

Reaction notes

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