Hydrochloric Acid → HCID 21463032, compound

HRID 1940972Notes

Reaction equation

HRID 1940972 reaction equation
C([O:3][C:4]([C:6]1[C:7](=[O:23])[O:8][C:9]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][C:10]=2[C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:5])C.OC1C=CC(C)=CC=1C(C1C=CC=CC=1)=O.C(OCC)(=O)CC(OCC)=O.N12CCCN=C1CCCCC2.Cl>C(O)(=O)C>[CH3:22][C:19]1[CH:20]=[CH:21][C:9]2[O:8][C:7](=[O:23])[C:6]([C:4]([OH:5])=[O:3])=[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:10]=2[CH:18]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 7761Diethyl MalonateHCID 738512-Hydroxy-5-methylbenzophenoneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 54292911HCID 54292911, compound

Product 1

HCID 21463032HCID 21463032, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 6-methyl-2-oxo-4-phenyl-2H-1-benzopyran-3-carboxylic acid ethyl ester [prepared by heating 2-hydroxy-5-methylbenzophenone and diethyl malonate in the presence of 1,8-diazabicyclo[5.4.0]undec-7-en; melting point: 129°-131° C.; NMR (200 MHz, CDCl3) ppm: 0.96 (3H, t, J=7.2 Hz), 2.31 (3H, s), 4.07 (2H, q, J=7.2 Hz), 7.01 (1H, bs), 7.2-7.4 (4H, m), 7.5-7.6 (3H, m)] (10.0 g), acetic acid (100 ml). and hydrochloric acid (60 ml) was heated under reflux at 110° C. for 15 hours. After the solvent was distilled off, ethyl acetate was added to the residue. The mixture was washed with water and dried, after which the solvent was distilled off, to yield 6-methyl-2-oxo-4-phenyl-2H-1-benzopyran-3-carboxylic acid as colorless crystals (8.7 g).

Workup

  1. customprepared
  2. distillationAfter the solvent was distilled off
  3. additionethyl acetate was added to the residue
  4. washThe mixture was washed with water
  5. customdried
  6. distillationafter which the solvent was distilled off

Sources & evidence

ORD record
ord-a36bc1b222704379aaa3045026705c8f
Source dataset
uspto-grants-1997_12
Patent number
US05700810

Reaction notes

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