Benzaldehyde → Hexyl hexanoate
Reaction equation
[CH:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1(C)C=CC=CC=1>[CH2:1]([OH:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[C:1]([O:8][CH2:1][CH2:2][CH2:7][CH2:6][CH2:5][CH3:4])(=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]Participants
Reactant 1
Product 2
Reagents, catalysts & solvents 1
Procedure
When a toluene solution of benzyl alcohol and 0.1% complex 2′ was refluxed for 24 hrs in an open system, benzyl benzoate was formed in 70% yield, accompanied by a small amount of benzaldehyde (4%) (Table 24, entry 1). Refluxing 1-hexanol with 0.1% 2 in toluene (115° C.) or neat (157° C.) for 24 hrs resulted in formation of 60-70% of hexyl hexanoate, accompanied by 2.5-10% hexanal (Table 24, entries 2 and 3). Complex 6′ was slightly less catalytically active than 2 (Table 24, entry 7). The PNN complex 4′ exhibited significantly higher catalytic activity than that of the PNP complexes 2′ and 6′; benzyl alcohol, 1-hexanol and 1-butanol were dehydrogenated to the corresponding esters in over 90% yield after heating with 0.1% 4′ in toluene (Table 24, entry 4-6).
Sources & evidence
- ORD record
- ord-d9de3cf38f3d4453b933e68bde24dfc1
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09045381B2
Reaction notes
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