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Hydrochloric Acid → 7-hydroxy-3-(4-hydroxyphenyl)-2H-chromen-2-one

HRID 2171749
Notes
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Reaction equation

HRID 2171749 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:12](=[O:25])[O:13][C:14]3[C:19]([CH:20]=2)=[CH:18][CH:17]=[C:16]([O:21]C(=O)C)[CH:15]=3)=[CH:7][CH:6]=1)(=O)C.[OH-].[Li+].O.Cl>CN(C=O)C>[OH:21][C:16]1[CH:15]=[C:14]2[C:19]([CH:20]=[C:11]([C:8]3[CH:9]=[CH:10][C:5]([OH:4])=[CH:6][CH:7]=3)[C:12](=[O:25])[O:13]2)=[CH:18][CH:17]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 3840254-[7-(acetyloxy)-2-oxo-2H-chromen-3-yl]phenyl acetate2×

Product 1

HCID 102440187-hydroxy-3-(4-hydroxyphenyl)-2H-chromen-2-one

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
65 °C

Procedure

To a solution of 4-(7-acetoxy-2-oxo-2H-chromen-3-yl)phenyl acetate of formula (3) (80 gm) in DMF (400 mL) an aqueous solution of lithium hydroxide (29.8 g, 0.71 mol) was added at RT and maintained at 60-70° C. for 1-2 hours. After the completion of the reaction, water (800 mL) and dilute hydrochloric acid (112 mL) was added to the reaction mass. The reaction mass was maintained at RT for 1-2 hours. The solid was filtered and dried at 70-75° C. for 6-8 hours to afford the title compound.

Workup

  1. additionwas added to the reaction mass
  2. temperatureThe reaction mass was maintained at RT for 1-2 hours
  3. filtrationThe solid was filtered
  4. customdried at 70-75° C. for 6-8 hours

Sources & evidence

ORD record
ord-50ef238a170741f48bf7e58b3a09d8d9
Source dataset
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09051291B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes