Phthalaldehydic acid → Benzoic acid, 2-formyl-, 3,7-dimethyl-6-octenyl ester

HRID 495335Notes

Reaction equation

HRID 495335 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][CH:18]([CH2:20][CH2:21]O)[CH3:19])[CH3:14].C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[CH:1]([C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([O:7][CH2:21][CH2:20][CH:18]([CH3:19])[CH2:17][CH2:16][CH:15]=[C:13]([CH3:14])[CH3:12])=[O:6])=[O:2]

Participants

5

Reactant 3

HCID 8406Phthalaldehydic acidHCID 8842CitronellolHCID 10868Dicyclohexylcarbodiimide

Product 1

HCID 10613355Benzoic acid, 2-formyl-, 3,7-dimethyl-6-octenyl esterYield 16%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 7.50 g (50.0 mmol) 2-formylbenzoic acid, 4.88 g (40.0 mmol) 4-dimethyl aminopyridine (DMAP) and 15.60 g (100.0 mmol) citronellol in 75 ml dichloromethane was cooled in an ice bath before addition of a solution of 11.35 g (55.0 mmol) dicyclohexylcarbodiimide (DCC) in 25 ml dichloromethane for 15 min. The reaction medium was maintained with 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×). The organic phase was dried over Na2SO4, concentrated and chromatographed twice (SiO2, ethyl toluene/ethyl acetate 19:1 and SiO2, toluene) to give 2.25 g (16%) 3,7 dimethyl-6-octenyl 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×)
  6. dry with materialThe organic phase was dried over Na2SO4
  7. concentrationconcentrated
  8. customchromatographed twice (SiO2, ethyl toluene/ethyl acetate 19:1 and SiO2, toluene)

Sources & evidence

ORD record
ord-bc41448e331d4d659aba78c2d7096f18
Source dataset
uspto-grants-2005_09
Patent number
US06939835B2

Reaction notes

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