Sodium Hydroxide → 5-Phenylfuran-2-carboxylic acid

HRID 659114

Reaction equation

HRID 659114 reaction equation
[C:1]1([C:7]2[O:11][C:10]([CH:12]=[O:13])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-:14].[Na+]>[N+]([O-])([O-])=O.[Ag+]>[C:1]1([C:7]2[O:11][C:10]([C:12]([OH:14])=[O:13])=[CH:9][CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 27694205-Phenyl-2-furaldehyde

Product 1

HCID 7362555-Phenylfuran-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 24470Silver NitrateCatalyst

Conditions

Temperature
60 °C

Procedure

To 5-phenyl-2-furaldehyde (35) (690 mg, 4.01 mmol) was added solid NaOH (176 mg, 4.40 mmol) then 10% NaOH solution (6.2 mL). Silver nitrate (680 mg, 4.00 mmol) was added and the reaction mixture heated to 60° C. for 4.5 hours then cooled to ambient temperature. The reaction mixture was then filtered and washed with water. The filtrate was acidified to pH 2 using 2N HCl and the precipitated product filtered and dried to give the title compound.

Workup

  1. temperaturethen cooled to ambient temperature
  2. filtrationThe reaction mixture was then filtered
  3. washwashed with water
  4. filtrationthe precipitated product filtered
  5. customdried

Sources & evidence

ORD record
ord-fe5a9621d48b45708e5f897cbdb23907
Source dataset
uspto-grants-2011_12
Patent number
US08080567B2

Linked notes

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