2-Ethyl-1-butanol → 2-Ethylbutyl hexanoate

HRID 1522958Notes

Reaction equation

HRID 1522958 reaction equation
[C:1]([OH:8])(=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[CH2:9]([CH:11]([CH2:14][CH3:15])[CH2:12]O)[CH3:10]>C([O-])(=O)C([O-])=O.[Sn+4].C([O-])(=O)C([O-])=O.O>[C:1]([O:8][CH2:12][CH:11]([CH2:14][CH3:15])[CH2:9][CH3:10])(=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 2

HCID 73582-Ethyl-1-butanolHCID 8892Hexanoic Acid

Product 1

HCID 2223492-Ethylbutyl hexanoateYield 87.9%

Reagents, catalysts & solvents 2

HCID 9839089Oxalate;tin(4+)CatalystHCID 962WaterSolvent

Conditions

Temperature
10 °C

Procedure

580.8 g (5 mol) of caproic acid, 613.1 g (6 mol) of 2-ethylbutanol and 0.34 g of tin oxalate (“Fascat 2001”) were heated to 160° C. under N2, during which water separation was observed. Once water separation had subsided, the mixture was heated to 210° C. in 10° C. steps. This temperature was then held for 3 h. Then, firstly the excess alcohol was removed by distillation and then the product was distilled at 13-31 mbar and 114-124° C. The product (879.9 g) was obtained as a clear liquid with an acid number of 0.26 and an OH number of 2.17.

Workup

  1. customOnce water separation
  2. customThen, firstly the excess alcohol was removed by distillation
  3. distillationthe product was distilled at 13-31 mbar and 114-124° C

Sources & evidence

ORD record
ord-3c32bf551c374ffaa4768054be01267e
Source dataset
uspto-grants-2015_07
Patent number
US09079850B2

Reaction notes

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