Formic Acid → Hexyl 4-oxopentanoate

HRID 860911Notes

Reaction equation

HRID 860911 reaction equation
[C:1]([OH:8])(=[O:7])[CH2:2][CH2:3][C:4]([CH3:6])=[O:5].C(O)=O.[C:12]1(C)[C:13](S(O)(=O)=O)=[CH:14][CH:15]=[CH:16][CH:17]=1.C=CCCCC>>[C:1]([O:8][CH2:14][CH2:13][CH2:12][CH2:17][CH2:16][CH3:15])(=[O:7])[CH2:2][CH2:3][C:4]([CH3:6])=[O:5]

Participants

5

Reactant 4

HCID 284Formic AcidHCID 69252-Methylbenzenesulfonic acidHCID 11579Levulinic AcidHCID 115971-Hexene2×

Product 1

HCID 14745448Hexyl 4-oxopentanoate

Conditions

Temperature
100 °C

Procedure

A 5 cc autoclave is charged with 2 cc of an aqueous solution containing 2 mmoles of levulinic acid and 0.2 mmoles of formic acid. 3 wt. % toluene sulfonic acid is added as a catalyst. The reactor is pressurized to 0.69 MPa with 1-hexene and heated to 100° C. for 2 hours while maintaining a constant pressure of 1-hexene. After cooling, the organic phase is separated. A mixture of hexyl formate and hexyl levulinate is formed as product.

Workup

  1. temperatureAfter cooling
  2. customthe organic phase is separated
  3. additionA mixture of hexyl formate

Sources & evidence

ORD record
ord-5789ab5f875b4040bc4ab8b339c74fdd
Source dataset
uspto-grants-2006_12
Patent number
US07153996B2

Reaction notes

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