Potassium Hydroxide → HCID 67895409, compound

HRID 231488Notes

Reaction equation

HRID 231488 reaction equation
C[O:2][C:3](=[O:16])[CH2:4][CH:5]1[O:9][C:8]2[CH:10]=[CH:11][C:12]([O:14][CH3:15])=[CH:13][C:7]=2[CH2:6]1.[OH-].[K+]>C(O)C.O>[CH3:15][O:14][C:12]1[CH:11]=[CH:10][C:8]2[O:9][CH:5]([CH2:4][C:3]([OH:16])=[O:2])[CH2:6][C:7]=2[CH:13]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 58051386HCID 58051386, compound

Product 1

HCID 67895409HCID 67895409, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

110 g of 5-methoxy-2,3-dihydro-3-benzofuranacetic acid methylester dissolved in 400 ml of ethanol were added during 20 minutes to a solution of 55 g of KOH in 70 ml of water and 500 ml of ethanol at reflux temperature. Reflux was continued for 0.5 hours. Ethanol was evaporated and 600 ml of water were added, and the mixture was acidified with cold conc. hydrochloric acid and subsequently extracted with dichloromethane (3×300 ml). The combined organic phases were washed with brine, dried (MgSO4) and evaporated to a volume of 200 ml. 700 ml of n-heptane were added, and excess dichloromethane evaporated. The mixture was cooled to 0° C., and the precipitated carboxylic acid filtered off. Yield: 91 g. M.P. 111°-112° C.

Workup

  1. temperatureat reflux temperature
  2. temperatureReflux
  3. customEthanol was evaporated
  4. addition600 ml of water were added
  5. extractionsubsequently extracted with dichloromethane (3×300 ml)
  6. washThe combined organic phases were washed with brine
  7. dry with materialdried (MgSO4)
  8. customevaporated to a volume of 200 ml
  9. addition700 ml of n-heptane were added
  10. customexcess dichloromethane evaporated
  11. filtrationthe precipitated carboxylic acid filtered off

Sources & evidence

ORD record
ord-208e76fa395c4318a45654ac048acff3
Source dataset
uspto-grants-1989_07
Patent number
US04847254

Reaction notes

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