Hydrochloric Acid → HCID 12926038, compound

HRID 894633Notes

Reaction equation

HRID 894633 reaction equation
[C:1]([C:4]1[CH:15]=[CH:14][C:7]2[O:8][C:9]3([C:12](=[O:13])[C:6]=2[CH:5]=1)[CH2:11][CH2:10]3)(=[O:3])C.Cl[O-].[Na+].S([O-])(O)=[O:20].[Na+].Cl>O>[C:1]([C:4]1[CH:15]=[CH:14][C:7]2[O:8][C:9]3([C:12](=[O:13])[C:6]=2[CH:5]=1)[CH2:11][CH2:10]3)([OH:3])=[O:20]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 717555-Acetylspiro(benzofuran-2(3H),1'-cyclopropan)-3-oneHCID 23665760Sodium HypochloriteHCID 23665763Sodium BisulfiteHCID 178435167HCID 178435167, compound

Product 1

HCID 12926038HCID 12926038, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

5-Acetylspiro[benzo[b]furan-2(3H),1'-cyclopropane]-3-one (13.5 g.) was added to 300 ml. of aqueous solution of sodium hypochlorite. To the mixture was further added a small amount of surface active agent (polyoxyethylene octyl phenyl ether), and the mixture was stirred at 60° C. for 3 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 collected by filtration. After washing with water and drying, the crystals were recrystallized from ethanol to give colorless needles of 5-carboxyspiro[benzo[b]furan-2(3H),1'-cyclopropane]-3-one (12.68 g.). m.p. 215°-228° C.

Workup

  1. temperatureAfter cooling
  2. customresulting crystals
  3. filtrationwere collected by filtration
  4. washAfter washing with water
  5. customdrying
  6. customthe crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-e8eceba956a94f3e90b48c826c845271
Source dataset
uspto-grants-1981_08
Patent number
US04284644

Reaction notes

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