Hydrochloric Acid → 6,7-dimethoxy-1,4-dihydro-3H-isochromen-3-one

HRID 1297090Notes

Reaction equation

HRID 1297090 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][C:12]([OH:14])=[O:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[CH2:15]=O.Cl>CC(O)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:6](=[CH:7][C:8]=1[O:9][CH3:10])[CH2:15][O:13][C:12](=[O:14])[CH2:11]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 7139(3,4-Dimethoxyphenyl)acetic acid

Product 1

HCID 3356106,7-dimethoxy-1,4-dihydro-3H-isochromen-3-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
120 °C

Procedure

Heat at 120° C. for 1 hour a mixture of 19.6 g (100 mmol) of 3,4-dimethoxyphenyl acetic acid (VII), 7.4 g (246 mmol) of paraformaldehyde and 20 ml of concentrated HCl in 100 ml of AcOH. Evaporate to dryness. Add 100 ml of H2O, and extract three times with 200 ml of CH2Cl2. Wash the organic phases with 50 ml of 0.5 N NaHCO3 and dry on Na2SO4. Evaporate to dryness. Allow to crystallize for 2 hours in 50 ml of Et2O.

Workup

  1. customEvaporate to dryness
  2. additionAdd 100 ml of H2O
  3. extractionextract three times with 200 ml of CH2Cl2
  4. washWash the organic phases with 50 ml of 0.5 N NaHCO3
  5. customdry on Na2SO4
  6. customEvaporate to dryness
  7. customto crystallize for 2 hours in 50 ml of Et2O

Sources & evidence

ORD record
ord-4e5d3c37c9b547a9b7ef82ad4194e70d
Source dataset
uspto-grants-2007_07
Patent number
US07250410B2

Reaction notes

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