Hydrochloric Acid → HCID 19022304, compound

HRID 257669Notes

Reaction equation

HRID 257669 reaction equation
[C:1]([C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[C:17]([OH:19])=[CH:16][CH:15]=[CH:14]2)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.NN.[OH-].[Na+].Cl.C(O)[CH2:27][O:28]CCO>O>[CH2:1]([C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[C:17]([OH:19])=[C:16]([O:28][CH3:27])[CH:15]=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8117Diethylene GlycolHCID 14798Sodium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 19022310HCID 19022310, compound

Product 1

HCID 19022304HCID 19022304, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

122 g of 8-benzoyl-1-naphthol was suspended in 800 ml of diethylene glycol, followed by the addition of 250 ml of hydrazine monohydrate and 99 g of sodium hydroxide at room temperature. The obtained mixture was stirred at 100° C. for 48 hours and cooled to room temperature by allowing to stand, followed by the addition of 500 ml of water. The obtained mixture was acidified with concentrated hydrochloric acid and extracted with 1.5 l of toluene. The organic layer was washed with a saturated aqueous solution of sodium chloride and purified by silica gel column chromatography (developer: benzene) to give 100 g of the title compound as a pale-yellow crystal.

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted with 1.5 l of toluene
  3. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  4. custompurified by silica gel column chromatography (developer: benzene)

Sources & evidence

ORD record
ord-e06e517c7cf447dbbdcc998ce4393bb0
Source dataset
uspto-grants-1993_11
Patent number
US05262565

Reaction notes

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