Sodium Hydroxide → HCID 12802807, compound

HRID 1448819Notes

Reaction equation

HRID 1448819 reaction equation
[O:1]=[C:2]1[CH:11]=[C:10]([CH:12](C(OCC)=O)[C:13]([O:15]CC)=[O:14])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[OH-].[Na+]>C(O)C.O>[O:1]=[C:2]1[CH:11]=[C:10]([CH2:12][C:13]([OH:15])=[O:14])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 20375644HCID 20375644, compound

Product 1

HCID 12802807HCID 12802807, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

Diethyl 1,2-dihydro-2-oxo-1-phenylquinol-4-ylmalonate (2.7 g.) was dissolved in ethanol (50 ml.), and a solution of sodium hydroxide (2.85 g.) in water (3 ml.) was added. The mixture was heated under reflux for 1 hour, and then cooled and poured into water (200 ml.) to give a solution which was treated with decolourising carbon, filtered, and adjusted to pH 3 by addition of hydrochloric acid. The precipitate was collected by filtration, washed with water, drained, and crystallised from methanol to give 1,2-dihydro-2-oxo-1-phenylquinol-4-ylacetic acid, m.p. 185.5°-186° C. (decomposition), in 51% yield.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 1 hour
  3. temperaturecooled
  4. customto give a solution which
  5. additionwas treated with decolourising carbon
  6. filtrationfiltered
  7. additionadjusted to pH 3 by addition of hydrochloric acid
  8. filtrationThe precipitate was collected by filtration
  9. washwashed with water
  10. customcrystallised from methanol

Sources & evidence

ORD record
ord-b28b1593246e4162b25d4a32bd7abe70
Source dataset
uspto-grants-1980_02
Patent number
US04187310

Reaction notes

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