Pyridine → 5,5-Dimethyl-3-oxocyclohex-1-en-1-yl butanoate

HRID 325257Notes

Reaction equation

HRID 325257 reaction equation
[CH3:1][C:2]1([CH3:10])[CH2:9][C:7](=[O:8])[CH2:6][C:4](=[O:5])[CH2:3]1.N1C=CC=CC=1.[C:17](Cl)(=[O:21])[CH2:18][CH2:19][CH3:20]>C(Cl)Cl>[C:17]([O:5][C:4]1[CH2:3][C:2]([CH3:10])([CH3:1])[CH2:9][C:7](=[O:8])[CH:6]=1)(=[O:21])[CH2:18][CH2:19][CH3:20]

Participants

5

Reactant 3

HCID 1049PyridineHCID 8855Butyryl chlorideHCID 31358Dimedone

Product 1

HCID 124543575,5-Dimethyl-3-oxocyclohex-1-en-1-yl butanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dimedone (5,5-dimethylcyclohexane-1,3-dione, 99%, 14.2 g), pyridine (9 ml) and methylene chloride (100 ml) were mixed in a flask and butyryl chloride (11.4 g) was added dropwise. The mixture was stirred for 26 hours at room temperature and filtered. The filtrate was washed with HCl (6 N, 100 ml), water (100 ml), saturated Na2CO3 (50 ml), water (50 ml), dried (MgSO4). The solvent was removed under reduced pressure to yield 3-butyroxy-5,5-dimethylcyclohex-2-en-1-one as a yellow liquid.

Workup

  1. filtrationfiltered
  2. washThe filtrate was washed with HCl (6 N, 100 ml), water (100 ml), saturated Na2CO3 (50 ml), water (50 ml)
  3. dry with materialdried (MgSO4)
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-21984b9af0734265bf55c410384dcb5f
Source dataset
uspto-grants-1984_04
Patent number
US04440566

Reaction notes

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