Oxalyl chloride → naphtho[1,2-b]furan-3(2H)-one

HRID 847235Notes

Reaction equation

HRID 847235 reaction equation
[C:1]1([O:11][CH2:12][C:13]([OH:15])=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)C(Cl)=O.[Cl-].[Al+3].[Cl-].[Cl-]>C1C=CC=CC=1>[O:11]1[CH2:12][C:13](=[O:15])[C:2]2[CH:3]=[CH:4][C:5]3[C:10]([C:1]1=2)=[CH:9][CH:8]=[CH:7][CH:6]=3

Participants

5

Reactant 3

HCID 65578Oxalyl chlorideHCID 76313Naphthoxyacetic acidHCID 6451240Aluminum(III) Chloride

Product 1

HCID 1471593naphtho[1,2-b]furan-3(2H)-oneYield 84.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 2-(1-naphthoxy)acetic acid (2.26 g, 11.2 mmol) in benzene (20 mL) was added oxalyl chloride (5 mL, 57.3 mmol). The resulting mixture was heated at reflux for 30 min, then allowed to cool and concentrated under reduced pressure. The residue was dissolved in benzene, and to this was added aluminium chloride (1.83 g, 13.9 mmol). The resulting mixture was stirred at room temperature for 1 h, then poured into ice. The organic phase was separated and washed with saturated aqueous NaCl. Removal of the solvent in vacuo provided the title compound (1.74 g, 84%).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 30 min
  3. temperatureto cool
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue was dissolved in benzene
  6. additionpoured into ice
  7. customThe organic phase was separated
  8. washwashed with saturated aqueous NaCl
  9. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-03e4a1d82c734ab1a2b4bc25f0272fba
Source dataset
uspto-grants-1992_08
Patent number
US05140047

Reaction notes

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