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

HRID 1259273Notes

Reaction equation

HRID 1259273 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-6e324b74d5464af0a99b826eaaf0fbc9
Source dataset
uspto-grants-2013_06
Patent number
US08466150B2

Reaction notes

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