Formaldehyde → 5,6-Dimethoxy-3H-isobenzofuran-1-one

HRID 1881206Notes

Reaction equation

HRID 1881206 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[C:6]([OH:8])=[O:7].[CH2:14]=O>Cl>[CH3:13][O:12][C:11]1[CH:10]=[C:9]2[C:5](=[CH:4][C:3]=1[O:2][CH3:1])[C:6](=[O:8])[O:7][CH2:14]2

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 7121Veratric Acid

Product 1

HCID 2304605,6-Dimethoxy-3H-isobenzofuran-1-one

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 3,4-dimethoxy-benzoic acid (10 g) in 37% HCl (150 ml) and formaldehyde (25 ml, 37 wt. % solution in water) was heated to 90° C. for 4¾ hours, and then insoluble material was removed by filtration. The filtrate was quenched with water (200 ml) and extracted three times with ethyl acetate (200 ml). The combined organic layers were washed with aqueous NaOH (40 ml, 2.5 M) and water (100 ml). The organic solvent was dried over anhydrous Na2SO4, filtered and evaporated to dryness

Workup

  1. custominsoluble material was removed by filtration
  2. customThe filtrate was quenched with water (200 ml)
  3. extractionextracted three times with ethyl acetate (200 ml)
  4. washThe combined organic layers were washed with aqueous NaOH (40 ml, 2.5 M) and water (100 ml)
  5. dry with materialThe organic solvent was dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-97bf5c88d8304169a9a2bbb26f01eab1
Source dataset
uspto-grants-2012_11
Patent number
US08318785B2

Reaction notes

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