Pyridine → 4-[(3,7-Dimethyloct-6-en-1-yl)oxy]-4-oxobutanoic acid

HRID 325133Notes

Reaction equation

HRID 325133 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH2:3][CH2:2]1.[CH3:8][C:9](=[CH:11][CH2:12][CH2:13][CH:14]([CH2:16][CH2:17][OH:18])[CH3:15])[CH3:10].N1C=CC=CC=1.CCOCC>CN(C)C1C=CN=CC=1.ClCCl>[CH3:15][CH:14]([CH2:13][CH2:12][CH:11]=[C:9]([CH3:8])[CH3:10])[CH2:16][CH2:17][O:18][C:4](=[O:5])[CH2:3][CH2:2][C:1]([OH:6])=[O:7]

Participants

7

Reactant 4

HCID 1049PyridineHCID 3283Diethyl EtherHCID 7922Succinic anhydrideHCID 8842Citronellol

Product 1

HCID 111728904-[(3,7-Dimethyloct-6-en-1-yl)oxy]-4-oxobutanoic acidYield 47.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 30.0 g succinic anhydride, 46.9 g citronellol, 36.0 g pyridine and 2.2 g 4-dimethylaminopyridine in 300 ml of dichloromethane was refluxed for 22 hours. Then the solution was cooled, ether was added and the organic phase was washed with 2N HCl and water to neutrality, dried and evaporated to dryness. The residue was wipe-film distilled to yield 36.4 g of a colourless liquid.

Workup

  1. temperatureThen the solution was cooled
  2. washthe organic phase was washed with 2N HCl and water to neutrality
  3. customdried
  4. customevaporated to dryness
  5. distillationThe residue was wipe-film distilled

Sources & evidence

ORD record
ord-2000d329f73a489cbf748caafef42bc8
Source dataset
uspto-grants-2001_04
Patent number
US06222062B1

Reaction notes

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