Hydrochloric Acid → 4,5,6,7-Tetrahydro-3-hydroxy-1(3H)-isobenzofuranone

HRID 925060Notes

Reaction equation

HRID 925060 reaction equation
[C:1]12[C:10](=[O:11])[O:9][C:7](=[O:8])[C:2]=1[CH2:3][CH2:4][CH2:5][CH2:6]2.[BH4-].[Na+].Cl>O1CCCC1>[OH:11][CH:10]1[C:1]2[CH2:6][CH2:5][CH2:4][CH2:3][C:2]=2[C:7](=[O:8])[O:9]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 124753,4,5,6-Tetrahydrophthalic anhydrideHCID 4311764Sodium borohydride

Product 1

HCID 109097774,5,6,7-Tetrahydro-3-hydroxy-1(3H)-isobenzofuranone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-cyclohexene-1,2-dicarboxylic anhydride (25.2 g) in tetrahydrofuran (125 mL) at 0° C. was added sodium borohydride (1.51 g). The mixture was warmed to ambient temperature for 30 minutes, heated at reflux for 5 hours, cooled, treated with 1N hydrochloric acid and concentrated. The concentrate was partitioned between ethyl acetate and brine, and the organic layer was washed with brine and water and concentrated. The concentrate was purified by flash chromatography with 50% ethyl acetate in hexane.

Workup

  1. temperatureheated
  2. temperatureat reflux for 5 hours
  3. temperaturecooled
  4. concentrationconcentrated
  5. customThe concentrate was partitioned between ethyl acetate and brine
  6. washthe organic layer was washed with brine and water
  7. concentrationconcentrated
  8. customThe concentrate was purified by flash chromatography with 50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-21ad948c0b8e4a9facb190b2bce48c6e
Source dataset
uspto-grants-2016_03
Patent number
US09283222B2

Reaction notes

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