Ethanol → 2,3-Dihydro-5-(4-(1-hydroxyethyl)phenyl)-2-benzofurancarboxylic acid

HRID 1395684Notes

Reaction equation

HRID 1395684 reaction equation
C(O)C.[OH:4][CH:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:14]=[CH:15][C:16]3[O:20][C:19]([C:21]([O:23]CC)=[O:22])=[CH:18][C:17]=3[CH:26]=2)=[CH:9][CH:8]=1)[CH3:6]>O1CCCC1>[OH:4][CH:5]([C:7]1[CH:8]=[CH:9][C:10]([C:13]2[CH:14]=[CH:15][C:16]3[O:20][CH:19]([C:21]([OH:23])=[O:22])[CH2:18][C:17]=3[CH:26]=2)=[CH:11][CH:12]=1)[CH3:6]

Participants

4

Reactant 2

HCID 702EthanolHCID 20337913Ethyl 5-(4-(1-hydroxyethyl)phenyl)-2-benzofurancarboxylate

Product 1

HCID 203379082,3-Dihydro-5-(4-(1-hydroxyethyl)phenyl)-2-benzofurancarboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

75 ml of ethanol was added to a solution of 23.9 g of 6B in 300 ml of tetrahydrofuran, then 195.7 g of 2.5% sodium/mercury amalgam was added in portions, at room temperature. The mixture was stirred at room temperature overnight. The mercury was separated, the solid was collected and dissolved in 300 ml of water. The solution was acidified to pH=1 with concentrated hydrochloric acid. The solid was collected, washed with water and dried (P2O5 ; reduced pressure, 45° C.). The product was dissolved in tetrahydrofuran, the solution was filtered and its volume reduced to 30 ml by evaporating the solvent under reduced pressure. The resulting solution was triturated with ether. The solid was collected and dried in a vacuum oven over P2O5 to give 2,3-dihydro-5-(4-(1-hydroxyethyl)phenyl)-2-benzofurancarboxylic acid (6C), mp: 155°-157° C.

Workup

  1. customThe mercury was separated
  2. customthe solid was collected
  3. dissolutiondissolved in 300 ml of water
  4. customThe solid was collected
  5. washwashed with water
  6. dry with materialdried (P2O5 ; reduced pressure, 45° C.)
  7. dissolutionThe product was dissolved in tetrahydrofuran
  8. filtrationthe solution was filtered
  9. customby evaporating the solvent under reduced pressure
  10. customThe resulting solution was triturated with ether
  11. customThe solid was collected
  12. dry with materialdried in a vacuum oven over P2O5

Sources & evidence

ORD record
ord-66dc47013d4440c6a476c99db9f9c0e9
Source dataset
uspto-grants-1980_05
Patent number
US04205080

Reaction notes

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