Octanoic Acid → 2-Ethylbutyl octanoate

HRID 1522959Notes

Reaction equation

HRID 1522959 reaction equation
[C:1]([OH:10])(=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[CH2:11]([CH:13]([CH2:16][CH3:17])[CH2:14]O)[CH3:12]>C([O-])(=O)C([O-])=O.[Sn+4].C([O-])(=O)C([O-])=O.O>[C:1]([O:10][CH2:14][CH:13]([CH2:16][CH3:17])[CH2:11][CH3:12])(=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 2

HCID 379Octanoic AcidHCID 73582-Ethyl-1-butanol

Product 1

HCID 2298942-Ethylbutyl octanoateYield 76%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
10 °C

Procedure

187.2 g (1.3 mol) of caprylic acid, 214.0 g (2.09 mol) of 2-ethylbutanol and 0.14 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 8-12 mbar and 136-141° C. The product (225.6 g) was obtained as a clear liquid with an acid number of 0.47 and an OH number of 1.36.

Workup

  1. customOnce water separation
  2. customThen, firstly the excess alcohol was removed by distillation
  3. distillationthe product was distilled at 8-12 mbar and 136-141° C

Sources & evidence

ORD record
ord-c34136ba501744b982ddf3faad09fbd8
Source dataset
uspto-grants-2015_07
Patent number
US09079850B2

Reaction notes

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