Citronellol → HCID 10733156, compound

HRID 495339Notes

Reaction equation

HRID 495339 reaction equation
[C:1]([C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7])(=[O:3])[CH3:2].[CH3:13][C:14](=[CH:16][CH2:17][CH2:18][CH:19]([CH2:21][CH2:22]O)[CH3:20])[CH3:15].C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.ClCCl>[C:1]([C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([O:8][CH2:22][CH2:21][CH:19]([CH3:20])[CH2:18][CH2:17][CH:16]=[C:14]([CH3:15])[CH3:13])=[O:7])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 8842CitronellolHCID 10868DicyclohexylcarbodiimideHCID 684742-Acetylbenzoic acid

Product 1

HCID 10733156HCID 10733156, compoundYield 81.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 6.49 g (30.0 mmol) 2-acetylbenzoic acid, 3.81 g (31.2 mmol) DMAP and 12.48 g (80.0 mmol) citronellol in 60 ml dichloromethane was cooled in an ice bath before adding a solution of 8.84 g (42.9 mmol) DCC in 40 ml dichloromethane over 5 min. The reaction mixture was maintained with stirring at 40° for 75 h. The precipitate formed during the reaction was filtered and the filtrate washed with HCl (10%, 2×) and with a saturated Na2CO3 solution (2×). The organic phase was dried (Na2SO4), and the solvent evaporated. The excess citronellol was distilled (1 Torr, 60-80°), and the residue chromatographed (SiO2, 9:1 toluene/ethyl acetate) and distilled (0.6 Torr, 150-155°), to give 7.43 g (63%) of 3,7-dimethyl-6-octenyl 2-acetylbenzoate in the form of a colourless oil.

Workup

  1. temperatureThe reaction mixture was maintained
  2. customThe precipitate formed during the reaction
  3. filtrationwas filtered
  4. washthe filtrate washed with HCl (10%, 2×) and with a saturated Na2CO3 solution (2×)
  5. dry with materialThe organic phase was dried (Na2SO4)
  6. customthe solvent evaporated
  7. distillationThe excess citronellol was distilled (1 Torr, 60-80°)
  8. customthe residue chromatographed (SiO2, 9:1 toluene/ethyl acetate)
  9. distillationdistilled (0.6 Torr, 150-155°)

Sources & evidence

ORD record
ord-a994ae9501704c369b7be48ed9dc9deb
Source dataset
uspto-grants-2005_09
Patent number
US06939835B2

Reaction notes

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