Ethyl butyrate → 3-Pentanol, acetate (8CI)(9CI)

HRID 2167175Notes

Reaction equation

HRID 2167175 reaction equation
C(OCC)(=O)CCC.CCC(O)CC.[C:15]([O:20][CH:21]([CH2:24][CH3:25])[CH2:22][CH3:23])(=[O:19])[CH2:16]CC>C(O)C>[C:15]([O:20][CH:21]([CH2:24][CH3:25])[CH2:22][CH3:23])(=[O:19])[CH3:16]

Participants

5

Reactant 3

HCID 7762Ethyl butyrate2×HCID 114283-PentanolHCID 6428478HCID 6428478, compound

Product 1

HCID 692793-Pentanol, acetate (8CI)(9CI)

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

These reactions were also studied with unsymmetrical esters. The reaction of ethyl butyrate with 3-pentanol in the presence of 1 mol % of 1 under refluxing toluene led to 75% conversion of ethyl butyrate with the formation of 73% of 3-pentyl butyrate as the exclusive product (entry 16). Traces of 3-pentyl acetate, resulting from reaction with the formed ethanol, were also observed. The remaining ethanol probably evaporated from the reaction mixture under the reflux conditions. Similarly, the reaction of methyl hexanoate with cyclohexanol results in 42% conversion after 17 h with the formation of 42% of cyclohexyl hexanoate (entry 17).

Sources & evidence

ORD record
ord-1b41d79484d14cdd93d446bca622d88e
Source dataset
uspto-grants-2015_06
Patent number
US09045381B2

Reaction notes

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