Acetic Acid → HCID 58784962, compound

HRID 1375102Notes

Reaction equation

HRID 1375102 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[CH2:5][CH:6]([C:10](=[O:12])[CH3:11])[C:7](=[O:9])[CH3:8])[CH3:2].[C:14]([O:18][CH2:19][CH3:20])(=[O:17])[CH:15]=[CH2:16].C(O)(=O)C>N12CCCN=C1CCCCC2.C(OCC)C>[CH2:1]([O:3][C:4](=[O:13])[CH2:5][C:6]([C:7](=[O:9])[CH3:8])([C:10](=[O:12])[CH3:11])[CH2:16][CH2:15][C:14]([O:18][CH2:19][CH3:20])=[O:17])[CH3:2]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 8821Ethyl AcrylateHCID 87820Ethyl 3-acetyl-4-oxopentanoate

Product 1

HCID 58784962HCID 58784962, compoundYield 81.2%

Reagents, catalysts & solvents 2

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

Procedure

37 g of 3-acetyl-4-oxo-pentanoic acid ethyl ester, synthesized according to the procedure given in Example 15, and 0.3 g of 1,8-diazabicyclo-[5.4.0]-undec-7-ene were mixed, and 30 g of ethyl acrylate was added dropwise over 30 minutes. After stirring for 24 hours, the base was neutralized by adding acetic acid. 80 ml of diethyl ether was added, and the mixture was extracted with 60 ml of an aqueous sodium carbonate solution and 150 ml of water. Fractional distillation of the water-free organic layer yielded 46.2 g of 3,3-diacetyl-hexanedioic acid diethyl ester (boiling point: 150° C./0.03 mbar; purity: >99%; colorless).

Workup

  1. additionwere mixed
  2. extractionthe mixture was extracted with 60 ml of an aqueous sodium carbonate solution and 150 ml of water
  3. distillationFractional distillation of the water-free organic layer

Sources & evidence

ORD record
ord-a4aea11dd1d44f469542f68f53bc16a6
Source dataset
uspto-grants-2007_01
Patent number
US07166648B2

Reaction notes

Loading…