Phosphoric Acid → (5-fluoro-3,4-dihydro-1-oxo-2(1H)-naphthalenylidene)acetic acid

HRID 1457324Notes

Reaction equation

HRID 1457324 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][C:7]2=[O:12].O.[C:14]([OH:18])(=[O:17])[CH:15]=O.P(=O)(O)(O)O>O>[F:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][C:6](=[CH:15][C:14]([OH:18])=[O:17])[C:7]2=[O:12]

Participants

5

Reactant 3

HCID 1004Phosphoric AcidHCID 154910385-Fluoro-1,2,3,4-tetrahydronaphthalen-1-oneHCID 15620607Glyoxylic acid, monohydrate

Product 1

HCID 53647021(5-fluoro-3,4-dihydro-1-oxo-2(1H)-naphthalenylidene)acetic acidYield 96.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 5-fluoro-3,4-dihydro-1(2H)-naphthalenone (10 g), glyoxylic acid monohydrate (6.2 g) and 85% phosphoric acid (10 ml) was stirred at 90° C. for three hours. After cooling, water was added to the reaction solution, and the precipitated crystals were collected by filtration, washed with water, and dried to give (5-fluoro-3,4-dihydro-1-oxo-2(1H)-naphthalenylidene)acetic acid (13 g).

Workup

  1. temperatureAfter cooling
  2. filtrationthe precipitated crystals were collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-6e3cb22961d74446ab5cf94ced52ef73
Source dataset
uspto-grants-1998_12
Patent number
US05847159

Reaction notes

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