Acetic Acid → HCID 11064732, compound

HRID 2414244Notes

Reaction equation

HRID 2414244 reaction equation
[C:1]([CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])(=O)[CH2:2][CH2:3][CH3:4].[NH3:12].C(O)(=O)C.[C:17]1(=O)[CH:22]=[CH:21][C:20](=[O:23])[CH:19]=[CH:18]1>CO>[CH2:10]([O:9][C:7]([C:6]1[C:18]2[C:17](=[CH:22][CH:21]=[C:20]([OH:23])[CH:19]=2)[NH:12][C:1]=1[CH2:2][CH2:3][CH3:4])=[O:8])[CH3:11]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 222AmmoniaHCID 4650QuinoneHCID 238498Ethyl 3-oxohexanoate

Product 1

HCID 11064732HCID 11064732, compoundYield 6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Through a solution of ethyl butyrylacetate (23 g, 0.145 mol) in methanol (200 mL) was bubbled ammonia at 5° C. for 15 minutes and then stirred at room temperature for 24 hours. The reaction mixture was concentrated to about 20 mL. Acetic acid (150 mL) and 1,4-benzoquinone (15.7 g, 0.145 mol) was added to the reaction mixture and it was stirred for 3 hours at room temperature. The suspension that formed was filtered, washed with CH2Cl2 (2×50 mL), and the solid residue was dried in a vacuum oven at 50° C. for 24 hours to give the desired product (2.2 g, 6%). MS: 248.1 (M+1+).

Workup

  1. concentrationThe reaction mixture was concentrated to about 20 mL
  2. stirringwas stirred for 3 hours at room temperature
  3. customThe suspension that formed
  4. filtrationwas filtered
  5. washwashed with CH2Cl2 (2×50 mL)
  6. customthe solid residue was dried in a vacuum oven at 50° C. for 24 hours

Sources & evidence

ORD record
ord-2db28bcfab4b40aea6642f4f27dfd8d7
Source dataset
uspto-grants-2004_11
Patent number
US06812228B2

Reaction notes

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