Ethanol → 4-Benzofuranol

HRID 16408

Reaction equation

HRID 16408 reaction equation
[O:1]1[C:5]2[CH2:6][CH2:7][CH2:8][C:9](=[O:10])[C:4]=2[CH:3]=[CH:2]1.C(O)C>[Pd].C1C2C(CCCC2)CCC1.C=CCCCCCCCCCC>[O:1]1[C:5]2=[CH:6][CH:7]=[CH:8][C:9]([OH:10])=[C:4]2[CH:3]=[CH:2]1

Participants

6

Reactant 2

HCID 702EthanolHCID 27335414,5,6,7-Tetrahydro-1-benzofuran-4-one

Product 1

HCID 116079214-Benzofuranol

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 7044DecalinSolventHCID 81831-DodeceneSolvent

Conditions

Temperature
80 °C

Procedure

3.76 g (27.6 mmol) of 6,7-dihydro-1-benzofuran-4(5H)-one (prepared according to Tetrahedron Lett. 1994, 35, 6231) and 10% of palladium on activated carbon in 34 ml of decalin and 6 ml of dodecene are heated in a metal bath at 200° C. overnight. The mixture is cooled to 80° C., ethanol is added and the mixture is filtered off through CELITE (diatomaceous earth). The CELITE (diatomaceous earth) is washed twice with ethanol and the filtrate is concentrated. The residue, which still contains decalin and dodecene, is mixed with petroleum ether and cooled in an ice bath. An oily precipitate forms. The solvent is decanted off and the oil is purified by preparative HPLC.

Workup

  1. filtrationthe mixture is filtered off through CELITE (diatomaceous earth)
  2. washThe CELITE (diatomaceous earth) is washed twice with ethanol
  3. concentrationthe filtrate is concentrated
  4. additionThe residue, which still contains decalin and dodecene, is mixed with petroleum ether
  5. temperaturecooled in an ice bath
  6. customThe solvent is decanted off
  7. customthe oil is purified by preparative HPLC

Sources & evidence

ORD record
ord-e53e6d184e694ac9ab2df5d78b9d045c
Source dataset
uspto-grants-2010_06
Patent number
US07737153B2

Linked notes

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