Phthalaldehydic acid → HCID 10565146, compound

HRID 1356945Notes

Reaction equation

HRID 1356945 reaction equation
[CH:1]([C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=[O:6])=[O:2].[CH3:12][C:13](=[CH:15][CH2:16][CH2:17]/[C:18](=[CH:20]/[CH2:21]O)/[CH3:19])[CH3:14].C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.ClCCl>[CH:1]([C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([O:7][CH2:21]/[CH:20]=[C:18](\[CH3:19])/[CH2:17][CH2:16][CH:15]=[C:13]([CH3:14])[CH3:12])=[O:6])=[O:2]

Participants

6

Reactant 3

HCID 8406Phthalaldehydic acidHCID 10868DicyclohexylcarbodiimideHCID 637566Geraniol

Product 1

HCID 10565146HCID 10565146, compoundYield 22%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 7.50 g (50.0 mmol) 2-formylbenzoic acid, 4.89 g (40.0 mmol) DMAP and 15.42 g (100.0 mmol) geraniol in 75 ml dichloromethane was cooled in an ice bath before addition of a solution of 11.37 g (55.0 mmol) DCC in 25 ml dichloromethane, for 15 min. The reaction medium was maintained under stirring at 0° for 15 min, then at 20° for 48 h. The precipitate formed during the reaction was filtered and the filtrate washed with HCl (10%, 2×) and with a saturated Na2CO3 solution (2×) and water (2×). The organic phase was dried over Na2SO4, concentrated and chromatographed (SO2, 8:2 heptane/ether) to give 2.55 g (22%) (E)3,7-dimethyl-2,6-octadienyl 2-formylbenzoate in the pure state in the form of a colourless oil.

Workup

  1. temperatureThe reaction medium was maintained
  2. waitat 20° for 48 h
  3. customThe precipitate formed during the reaction
  4. filtrationwas filtered
  5. washthe filtrate washed with HCl (10%, 2×) and with a saturated Na2CO3 solution (2×) and water (2×)
  6. dry with materialThe organic phase was dried over Na2SO4
  7. concentrationconcentrated
  8. customchromatographed (SO2, 8:2 heptane/ether)

Sources & evidence

ORD record
ord-f6817d6f3a7f4dbf9d97fa35c45e1a56
Source dataset
uspto-grants-2003_07
Patent number
US06589921B2

Reaction notes

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