Acetic Acid → Hexanoic acid, 4-acetyl-5-oxo-, ethyl ester

HRID 1375112Notes

Reaction equation

HRID 1375112 reaction equation
[CH3:1][C:2](=[O:7])[CH2:3][C:4](=[O:6])[CH3:5].C(P(CCCCCCCC)CCCCCCCC)CCCCCCC.[C:33]([O:37][CH2:38][CH3:39])(=[O:36])[CH:34]=[CH2:35].C(O)(=O)C>C(OCC)C>[CH2:38]([O:37][C:33](=[O:36])[CH2:34][CH2:35][CH:3]([C:2](=[O:7])[CH3:1])[C:4](=[O:6])[CH3:5])[CH3:39]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8821Ethyl AcrylateHCID 20851TrioctylphosphineHCID 31261Acetylacetone

Product 1

HCID 2733934Hexanoic acid, 4-acetyl-5-oxo-, ethyl ester

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a mixture of 70 g of 2,4-pentandione and 1.72 g of trioctyl phosphine, 45 g of ethyl acrylate was added dropwise over 40 minutes, keeping the temperature at 0–5° C. by cooling. After stirring for 65 hours, 2 ml of acetic acid and 150 ml of diethyl ether were added, and the solution was extracted with an aqueous sodium carbonate solution and water. The organic layer was dried, and 4-acetyl-5-oxohexanoic acid ethyl ester was isolated by fractional distillation.

Workup

  1. additionwas added dropwise over 40 minutes
  2. customat 0–5° C.
  3. temperatureby cooling
  4. extractionthe solution was extracted with an aqueous sodium carbonate solution and water
  5. customThe organic layer was dried

Sources & evidence

ORD record
ord-5cd5095f06f6432781d64f504b667994
Source dataset
uspto-grants-2007_01
Patent number
US07166648B2

Reaction notes

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