Acetic Acid → HCID 21079436, compound

HRID 1375111Notes

Reaction equation

HRID 1375111 reaction equation
[C:1]([CH:4]([CH2:8][CH2:9][C:10](=[O:12])[CH3:11])[C:5](=[O:7])[CH3:6])(=[O:3])[CH3:2].[C:13]([O:17][CH2:18][CH3:19])(=[O:16])[CH:14]=[CH2:15].C(O)(=O)C>N12CCCN=C1CCCCC2.C(OCC)C>[CH2:18]([O:17][C:13](=[O:16])[CH2:14][CH2:15][C:4]([C:5](=[O:7])[CH3:6])([C:1](=[O:3])[CH3:2])[CH2:8][CH2:9][C:10](=[O:12])[CH3:11])[CH3:19]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 8821Ethyl AcrylateHCID 983523-Acetylheptane-2,6-dione

Product 1

HCID 21079436HCID 21079436, compoundYield 57.4%

Reagents, catalysts & solvents 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneCatalystHCID 3283Diethyl EtherSolvent

Procedure

10.2 g of 3-acetyl-2,6-heptandione and 5 drops of 1,8-diazabicyclo-[5.4.0]-undec-7-ene were mixed, and 9 g of ethyl acrylate was added dropwise over 15 minutes. After stirring for 16 hours, the base was neutralized with acetic acid, 30 ml of diethyl ether was added, and the solution was extracted with sodium carbonate solution and water. Fractional distillation of the dry organic layer yielded 9.3 g of 4,4-diacetyl-7-oxo-octanoic-ethyl ester (boiling point: 136° C./0.02 mbar; purity: 81%; colorless).

Workup

  1. additionwas added
  2. extractionthe solution was extracted with sodium carbonate solution and water
  3. distillationFractional distillation of the dry organic layer

Sources & evidence

ORD record
ord-67a4504da0024571ad82a2e22ed045d2
Source dataset
uspto-grants-2007_01
Patent number
US07166648B2

Reaction notes

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