Water → HCID 131717429, compound

HRID 893044Notes

Reaction equation

HRID 893044 reaction equation
O.[CH:2]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9](C=O)[C:4]=2[CH:3]=1.S(=O)(O)[O-:13].[Na+]>C(#N)C>[OH:13][C:5]12[CH:6]=[CH:7][CH:8]=[CH:9][CH:4]1[CH2:3][CH2:2]2

Participants

5

Reactant 3

HCID 962Water2×HCID 19894914HCID 19894914, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 131717429HCID 131717429, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

A solution of the thus prepared permonophosphoric acid (18 mL, 1.2M) in acetonitrile was added to a flask equipped with ice bath, stirrer and water-cooled condenser. To the stirred solution was added 3-benzocyclobutene aldehyde (5 g, 0.037 moles) dropwise over a period of 30 minutes. The reaction mixture was stirred for an additional 2 hours and cooled to 0° C. Water (20 mL) was added to the cooled reaction mixture, followed by the addition of sodium bisulfite solution until the reaction mixture was free from permonophosphoric acid, as tested with starch iodide paper. The organic solvent was removed by rotary evaporation, and sodium hydroxide was added until the reaction mixture became alkaline. The reaction mixture was cooled to 0° C., acidified and extracted with ethyl acetate. The organic layer was washed with water, sodium bicarbonate and brine. Drying and removal of the solvent was followed by flash chromatography using 10 percent ethyl acetate in hexanes to afford 3.19 g 3-hydroxybenzocyclobutene as a solid. This represents a yield of approximately 70 percent. The 3-benzocyclobutene phenol was recrystallized from pentane. The 3-benzocyclobutene phenol product has a melting point of 47° C. Product analysis indicated substantially complete conversion of 3-benzocyclobutene aldehyde with the product, other than the desired 3-hydroxybenzocyclobutene, comprising unidentified polymer-like substance with substantially no formation of 3-benzocyclobutene carboxylic acid.

Workup

  1. customequipped with ice bath, stirrer
  2. customThe organic solvent was removed by rotary evaporation, and sodium hydroxide
  3. additionwas added until the reaction mixture
  4. temperatureThe reaction mixture was cooled to 0° C.
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with water, sodium bicarbonate and brine
  7. customDrying
  8. customremoval of the solvent

Sources & evidence

ORD record
ord-eda9a0f37c454133b490964ef4e258c3
Source dataset
uspto-grants-1992_06
Patent number
US05120884

Reaction notes

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