Hydrochloric Acid → HCID 12961138, compound

HRID 261649Notes

Reaction equation

HRID 261649 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:18](=[O:22])[C:19]([OH:21])=[O:20])[CH:7]=[CH:8][C:9]=1[O:10]CC1C=CC=CC=1)([O-:3])=[O:2].Cl>C(O)(=O)C>[N+:1]([C:4]1[CH:5]=[C:6]([C:18](=[O:22])[C:19]([OH:21])=[O:20])[CH:7]=[CH:8][C:9]=1[OH:10])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 12961135HCID 12961135, compound

Product 1

HCID 12961138HCID 12961138, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-(3-nitro-4-benzyloxyphenyl)glyoxylic acid (30 g.), conc. hydrochloric acid (90 ml.) and acetic acid (120 ml.) was stirred for 3 hours at 100° C. To the reaction mixture was added under cooling ice-water (600 ml.) and the mixture was extracted with ethyl acetate. The extract was washed with ice-water, dried over magnesium sulfate and concentrated to dryness under reduced pressure. The residue was recrystallized from a mixture of benzene:ether:petroleum ether (2:1:4). The crystals were collected by filtration, washed with benzene and dried under reduced pressure to give 2-(3-nitro-4-hydroxyphenyl)glyoxylic acid (19.0 g.), mp 139° to 140.5° C.

Workup

  1. additionTo the reaction mixture was added under cooling ice-water (600 ml.)
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with ice-water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated to dryness under reduced pressure
  6. customThe residue was recrystallized from a mixture of benzene:ether:petroleum ether (2:1:4)
  7. filtrationThe crystals were collected by filtration
  8. washwashed with benzene
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-f24bbf5b7da74415893cdc9d644cb4b0
Source dataset
uspto-grants-1979_08
Patent number
US04166115

Reaction notes

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