methyl 4-methoxy-2-(2-methoxy-2-oxoethoxy)benzoate → HCID 54736958, compound

HRID 256340Notes

Reaction equation

HRID 256340 reaction equation
CC(C)([O-])C.[K+].[CH3:7][O:8][C:9]1[CH:18]=[CH:17][C:12]([C:13](OC)=[O:14])=[C:11]([O:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])[CH:10]=1>C1(C)C=CC=CC=1>[CH3:24][O:23][C:21]([C:20]1[O:19][C:11]2[CH:10]=[C:9]([O:8][CH3:7])[CH:18]=[CH:17][C:12]=2[C:13]=1[OH:14])=[O:22]

Participants

4

Reactant 2

HCID 736976methyl 4-methoxy-2-(2-methoxy-2-oxoethoxy)benzoateHCID 23665647Potassium tert-butoxide

Product 1

HCID 54736958HCID 54736958, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 10.4 g (0.093 mole) of potassium tert-butoxide in 175 ml of toluene (under a nitrogen atmosphere) is stirred and cooled in a cold water bath. A solution of 18.1 g (0.071 mole) of 4-methoxy-2-(2-methoxy-2-oxoethoxy) benzoic acid, methyl ester is added over 80 minutes. The mixture is stirred and heated on the steam bath for three hours, then cooled and added to 600 g of ice/water. The organic layer is separated, washed with water (2×100 ml), and the aqueous washes are combined with the original aqueous layer. The combined aqueous layers are washed with dichloromethane (2×250 ml), then filtered. The filtrate is cooled in ice and acidified with glacial acetic acid to precipitate the crude product, which is filtered and washed with water. Recrystallizatin from aqueous methanol yields 8.5 g 54% yield) of the 3-hydroxy-6-methoxy-2-benzofurancarboxylic acid methyl ester product, mp 93°-95 ° C. (mp of 80°-85° C. is reported in the J. D. Brewer, et al reference cited above).

Workup

  1. temperaturecooled in a cold water bath
  2. stirringThe mixture is stirred
  3. temperatureheated on the steam bath for three hours
  4. temperaturecooled
  5. customThe organic layer is separated
  6. washwashed with water (2×100 ml)
  7. washThe combined aqueous layers are washed with dichloromethane (2×250 ml)
  8. filtrationfiltered
  9. temperatureThe filtrate is cooled in ice
  10. customto precipitate the crude product, which
  11. filtrationis filtered
  12. washwashed with water

Sources & evidence

ORD record
ord-0c1f1f89993944f0abee36b86eaa1ff3
Source dataset
uspto-grants-1987_10
Patent number
US04703053

Reaction notes

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