Acetic Acid → 850785-06-7

HRID 2221350Notes

Reaction equation

HRID 2221350 reaction equation
[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.[CH3:13][C:14]([CH3:18])=[CH:15][CH:16]=O.C1(B(O)O)C=CC=CC=1.C(O)(=O)C>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:6]=[C:7]2[C:8](=[CH:9][CH:10]=1)[O:11][C:14]([CH3:18])([CH3:13])[CH:15]=[CH:16]2

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 610203-Methyl-2-butenalHCID 66827Phenylboronic AcidHCID 518900Benzeneacetic acid, 4-hydroxy-, methyl ester

Product 1

HCID 46918460850785-06-7

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

25 g methyl-4-hydroxyphenylacetate, 14.5 ml 3-methylbut-2-enal and 18.3 g phenylboronic acid were placed together under nitrogen atmosphere in 1 l dry toluene and heated to boiling for 7 hours under reflux cooling. Then 60 ml glacial acetic acid was added to this receiving solution at room temperature (=RT) and the mixture was again heated to boiling for 7 hours under reflux cooling. It was allowed to cool to room temperature, the solvent was largely evaporated at reduced pressure and the remaining residue was poured into 300 ml of a 1:1 (v/v) mixture of ethyl acetate (═EA) and water. The pH value was adjusted to 5 by addition of solid sodium bicarbonate, the organic phase was separated off and largely evaporated at reduced pressure. Chromatography of the remaining residue on silica gel (mobile phase: petroleum ether/EA 10:1 v/v) yielded 16 g methyl-(2,2-dimethyl-2H-chromen-6-yl)acetate as pale yellow oil.

Workup

  1. temperatureheated
  2. temperatureunder reflux
  3. temperaturecooling
  4. temperaturethe mixture was again heated
  5. waitto boiling for 7 hours
  6. temperatureunder reflux
  7. temperaturecooling
  8. customthe solvent was largely evaporated at reduced pressure
  9. additionthe remaining residue was poured into 300 ml of a 1:1 (v/v) mixture of ethyl acetate (═EA) and water
  10. additionThe pH value was adjusted to 5 by addition of solid sodium bicarbonate
  11. customthe organic phase was separated off
  12. customlargely evaporated at reduced pressure

Sources & evidence

ORD record
ord-0d45a24a4fd749528950fcc414bf145f
Source dataset
uspto-grants-2008_05
Patent number
US07368582B2

Reaction notes

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