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

HRID 749104Notes

Reaction equation

HRID 749104 reaction equation
[C:1]1(=[O:11])[O:6][C:4](=[O:5])[C:3]2[CH2:7][CH2:8][CH2:9][CH2:10][C:2]1=2.[BH4-].[Na+].Cl>O1CCCC1>[OH:11][CH:1]1[C:2]2[CH2:10][CH2:9][CH2:8][CH2:7][C:3]=2[C:4](=[O:5])[O:6]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)-isobenzofuranoneYield 53.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3,4,5,6-tetrahydrophthalic acid anhydride (10.0 g) in tetrahydrofuran (50.0 mL) was added sodium borohydride (600 mg) in ice bath. The mixture was stirred at room temperature for 30 minutes and refluxed for 5 hours. After cooling to room temperature, 1N hydrochloric acid (10.0 mL) was added to the reaction mixture, which was concentrated. Water was added to the residue, which was extracted with ethyl acetate. The extract was washed with water and brine sequentially, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:4) to give the title compound (5.40 g) having the following physical data.

Workup

  1. temperaturerefluxed for 5 hours
  2. temperatureAfter cooling to room temperature
  3. concentrationwas concentrated
  4. additionWater was added to the residue, which
  5. extractionwas extracted with ethyl acetate
  6. washThe extract was washed with water and brine sequentially
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated
  9. customThe residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:4)

Sources & evidence

ORD record
ord-7292adb0b1aa4923b80c84e5b99ceb74
Source dataset
uspto-grants-2008_07
Patent number
US07402580B2

Reaction notes

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