Acetic Acid → 4-METHOXYISOBENZOFURAN-1(3H)-ONE

HRID 2210049Notes

Reaction equation

HRID 2210049 reaction equation
[OH:1][C:2]1([C:11]([OH:13])=[O:12])[CH:10]=[CH:9][CH:8]=[CH:7][CH:3]1[C:4]([OH:6])=[O:5].[C:14](O)(=[O:16])C.[BH4-].[Na+].Cl>O1CCCC1>[CH3:14][O:1][C:2]1([C:11]([OH:13])=[O:12])[CH:10]=[CH:9][CH:8]=[CH:7][CH:3]1[C:4]([OH:6])=[O:5].[CH3:14][O:16][C:10]1[CH:9]=[CH:8][CH:7]=[C:3]2[C:2]=1[CH2:11][O:13][C:4]2=[O:6]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 22292283o-Hydroxyphthalsaure

Product 2

HCID 111163794-METHOXYISOBENZOFURAN-1(3H)-ONEHCID 19598034o-Methoxyphthalsaure

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Anhydrous 2-methoxyphthalic acid (640 mg), which was prepared with using anhydrous 2-hydroxyphthalic acid by the same procedure as reference example 12, was suspended in tetrahydrofuran (20 ml). Acetic acid (430 mg) and sodium borohydride (135 mg) were added to the suspension. The mixture was stirred for 30 min. at room temperature and for 2 hr. at 50° C. The reaction solution was cooled. 1N hydrochloric acid (7 ml) was added to the cooled solution. The solution was stirred for 15 min. The reaction solution was evaporated. The residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=2:1→1:1) to give the title compound (314 mg) having the following physical data.

Workup

  1. customat 50° C
  2. temperatureThe reaction solution was cooled
  3. stirringThe solution was stirred for 15 min
  4. customThe reaction solution was evaporated
  5. customThe residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=2:1→1:1)

Sources & evidence

ORD record
ord-1920310458944ed6910bb40d0ed2e10a
Source dataset
uspto-grants-1995_10
Patent number
US05457122

Reaction notes

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