Hydrochloric Acid → 7-carboxyspiro[benzo[b]furan-2(3H), 1'-cyclopropane]-3-one

HRID 66586Notes

Reaction equation

HRID 66586 reaction equation
[C:1]([C:4]1[C:9]2[O:10][C:11]3([C:14](=[O:15])[C:8]=2[CH:7]=[CH:6][CH:5]=1)[CH2:13][CH2:12]3)(=[O:3])C.Cl[O-].[Na+].S([O-])(O)=[O:20].[Na+].Cl>O>[C:1]([C:4]1[C:9]2[O:10][C:11]3([C:14](=[O:15])[C:8]=2[CH:7]=[CH:6][CH:5]=1)[CH2:13][CH2:12]3)([OH:3])=[O:20]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 3059949Spiro(benzofuran-2(3H),1'-cyclopropan)-3-one, 7-acetyl-HCID 23665760Sodium HypochloriteHCID 23665763Sodium BisulfiteHCID 178435167HCID 178435167, compound

Product 1

HCID 130372997-carboxyspiro[benzo[b]furan-2(3H), 1'-cyclopropane]-3-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 7-acetylspiro[benzo[b]furan-2(3H), 1'-cyclopropane]-3-one (86 mg), 2.4 ml of aqueous solution of sodium hypochlorite and a small amount of surface active agent (polyoxyethylene octyl phenyl ether) was stirred at 60° C. for 2 hours. After cooling, the reaction mixture was diluted with water, and to the mixture was added 40% aqueous solution of sodium hydrogen sulfite. The reaction mixture was made acidic with hydrochloric acid, and resulting crystals were extracted with ethyl acetate. After washing with water and drying, the solvent was distilled off under reduced pressure. The residue was recrystallized from ethanol to give colorless needles of 7-carboxyspiro[benzo[b]furan-2(3H), 1'-cyclopropane]-3-one. m.p. 259°-262° C. (decomp). Sublime at 183° C.

Workup

  1. temperatureAfter cooling
  2. customresulting crystals
  3. extractionwere extracted with ethyl acetate
  4. washAfter washing with water
  5. customdrying
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-3aba40a0980f483b8b62758edae7aae2
Source dataset
uspto-grants-1982_08
Patent number
US04342779

Reaction notes

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