3,4,5,6-Tetrahydrophthalic anhydride → 4,5,6,7-Tetrahydro-3-hydroxy-1(3H)-isobenzofuranone

HRID 925087Notes

Reaction equation

HRID 925087 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+]>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

4

Reactant 2

HCID 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, 165.6 mmol) in tetrahydrofuran (125 mL) placed in an ice bath was added sodium borohydride (1.51 g, 39.97 mmol). The ice bath was removed and the mixture was stirred at room temperature for 30 minutes, and under reflux for 5 hours. After cooling to room temperature, 1N HCl was added, and the reaction mixture concentrated. The residue was partitioned between ethyl acetate and brine. The organic layer was washed with brine, water and concentrated. The residue was purified by flash chromatography on silica gel eluting with 50% ethyl acetate in hexanes to provide the title compound. MS (ESI) m/z 155 (M+H)+.

Workup

  1. customThe ice bath was removed
  2. temperatureunder reflux for 5 hours
  3. temperatureAfter cooling to room temperature
  4. addition1N HCl was added
  5. concentrationthe reaction mixture concentrated
  6. customThe residue was partitioned between ethyl acetate and brine
  7. washThe organic layer was washed with brine, water
  8. concentrationconcentrated
  9. customThe residue was purified by flash chromatography on silica gel eluting with 50% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-03ad0001fb2847948c5250c69e667d33
Source dataset
uspto-grants-2016_03
Patent number
US09283222B2

Reaction notes

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