Hydrochloric Acid → 5,6-Dimethoxy-3H-isobenzofuran-1-one

HRID 1357017Notes

Reaction equation

HRID 1357017 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.[NH4+].[OH-]>O>[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

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 712FormaldehydeHCID 7121Veratric AcidHCID 14923Ammonium Hydroxide

Product 1

HCID 2304605,6-Dimethoxy-3H-isobenzofuran-1-oneYield 58.65%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under mechanical stirring a slurry of 3,4-dimethoxybenzoic acid (353.5 g, 1.94 moles) in HCHO (1.71, 24.5 moles) was prepared and cooled in ice, saturated with gaseous HCl (340 g, 9.32 moles), then gradually brought to 60° C. After 1 night the temperature was brought to room value and further HCl (300 g) was gurgled therein, then the temperature was brought to 60° C. again overnight. The mixture was brought to small volume, taken up in water (1 l), neutralized with 28% NH4OH (1.5 l) and kept at cold for 2 hours, then filtered. The filtrate was washed with water till neutrality, then crystallized from methanol (2 l) and dried under vacuum at 60° C. to give 220 g of the title product (yield: 58.65%).

Workup

  1. customwas prepared
  2. customgradually brought to 60° C
  3. customcold for 2 hours
  4. filtrationfiltered
  5. washThe filtrate was washed with water till neutrality,
  6. customthen crystallized from methanol (2 l)
  7. customdried under vacuum at 60° C.

Sources & evidence

ORD record
ord-ab96edfc5b494c3689a8d047a44e8983
Source dataset
uspto-grants-2003_07
Patent number
US06589951B1

Reaction notes

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