Propionic Acid → HCID 57093635, compound

HRID 1456929Notes

Reaction equation

HRID 1456929 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([OH:11])(=O)[CH2:8][CH3:9].O1[CH2:16][CH2:15][CH2:14][CH2:13]1>C(OCC)C>[CH:13]1[C:15]2[CH2:16][CH2:13][C:14]3[CH:16]=[CH:15][CH:14]=[CH:13][C:15]=3[CH:16]=[C:13]([CH2:9][CH2:8][CH2:7][OH:11])[C:14]=2[CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 1032Propionic AcidHCID 8028TetrahydrofuranHCID 21226445Aluminium lithium hydride

Product 1

HCID 57093635HCID 57093635, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of lithiumaluminum hydride (0.7 g, 18 mmol) in dry tetrahydrofuran (30 ml) the above propionic acid (2.6 g, 9.3 mmol) in dry diethyl ether (30 ml) was added. The reaction mixture was stirred at reflux temperature for 1.5 hour. The reaction was cooled on a ice bath and quenched by addition of water (0.7 ml), and 20% sodium hydroxide (0.7 ml), successively. The resulting mixture was filtered and the filtercake was washed with diethyl ether (2×100 ml). The phases were separated and the organic phase was evaporated in vacuo affording 2.6 g (100%) of 3-(11,12-dihydrodibenz[a,e]cycloocten-5-yl)-1-propanol as an oil.

Workup

  1. temperatureat reflux temperature for 1.5 hour
  2. temperatureThe reaction was cooled on a ice bath
  3. customquenched by addition of water (0.7 ml), and 20% sodium hydroxide (0.7 ml)
  4. filtrationThe resulting mixture was filtered
  5. washthe filtercake was washed with diethyl ether (2×100 ml)
  6. customThe phases were separated
  7. customthe organic phase was evaporated in vacuo

Sources & evidence

ORD record
ord-fe6686e05cef43848d3ca5e9c5bb35f1
Source dataset
uspto-grants-1998_12
Patent number
US05846968

Reaction notes

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