Ethanol → 2-Octanol

HRID 917899Notes

Reaction equation

HRID 917899 reaction equation
P.[CH3:2][C:3](=[O:10])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].C(O)C>O>[CH3:2][CH:3]([OH:10])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

5

Reactant 3

HCID 702EthanolHCID 80932-OctanoneHCID 24404Phosphine

Product 1

HCID 200832-Octanol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

Into a 3 ounce glass pressure bottle are placed 173 milligrams of [Rh(norbornadiene) (iso-propylmethylphenylphosphine)2 ]BF4 ([α]D25 = +11.0° for the phosphine), 8.2 grams of 2-octanone, 5 ml absolute ethanol, and 0.12 ml water. The bottle is flushed and filled with hydrogen as in Example 1 to 43 psig hydrogen. The bottle is warmed to 75°C and the contents stirred for 3.5 hours. The reaction mass is distilled to afford almost pure 2-octanol, [α]D25 = +0.15°, optical purity = 1.5%.

Workup

  1. customThe bottle is flushed
  2. distillationThe reaction mass is distilled

Sources & evidence

ORD record
ord-36028a132bc549bb9e7a8ffdc2982c2e
Source dataset
uspto-grants-1976_07
Patent number
US03968147

Reaction notes

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