2-Phenylethanol → HCID 10587030, compound

HRID 1356946Notes

Reaction equation

HRID 1356946 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].[C:12]1([CH2:18][CH2:19]O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.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][CH2:19][CH2:18][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:6])=[O:2]

Participants

6

Reactant 3

HCID 60542-PhenylethanolHCID 8406Phthalaldehydic acidHCID 10868Dicyclohexylcarbodiimide

Product 1

HCID 10587030HCID 10587030, compoundYield 11%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 12.72 g (84.8 mmol) 2-formylbenzoic acid, 8.27 g (67.8 mmol) DMAP and 20.69 g (169.6 mmol) 2-phenylethanol in 130 ml dichloromethane was cooled in an ice bath before adding a solution of 19.25 g (93.3 mmol) DCC in 40 ml dichloromethane for 10 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 with water (2×). The organic phase was dried over Na2SO4, concentrated and chromatographed (SiO2, 8:2 heptane/ether) to give 2.38 g (11%) 2-phenylethyl 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 with water (2×)
  6. dry with materialThe organic phase was dried over Na2SO4
  7. concentrationconcentrated
  8. customchromatographed (SiO2, 8:2 heptane/ether)

Sources & evidence

ORD record
ord-1373e1cc3bb34443b789ac66379817fa
Source dataset
uspto-grants-2003_07
Patent number
US06589921B2

Reaction notes

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