2-Phenylethanol → 5-Heptyl-2-oxo-tetrahydro-furan-3-carboxylic acid phenethyl ester

HRID 325130Notes

Reaction equation

HRID 325130 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH:8]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[O:7][C:6]1=[O:17])=[O:4].[C:18]1([CH2:24]CO)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CO>[CH2:1]([O:2][C:3]([CH:5]1[CH2:9][CH:8]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[O:7][C:6]1=[O:17])=[O:4])[CH2:24][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 60542-PhenylethanolHCID 154053805-Heptyl-2-oxo-tetrahydro-furan-3-carboxylic acid methylester

Product 1

HCID 537148545-Heptyl-2-oxo-tetrahydro-furan-3-carboxylic acid phenethyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 24.2 g 5-heptyl-2-oxo-tetrahydro-furan-3-carboxylic acid methyl ester, 24.4 g phenylethyl alcohol and 1.4 g tetraisopropyl-ortho-titanate was heated under nitrogen atmosphere to 130° C. for 5 minutes while methanol was distilled off. Then the reaction mixture was cooled to room temperature, poured into water and extracted with hexane. The organic layer was dried and evaporated to dryness. The residue was chromatographed to yield 23.9 g of a slightly yellow oil.

Workup

  1. distillationwas distilled off
  2. additionpoured into water
  3. extractionextracted with hexane
  4. customThe organic layer was dried
  5. customevaporated to dryness
  6. customThe residue was chromatographed
  7. customto yield 23.9 g of a slightly yellow oil

Sources & evidence

ORD record
ord-48ae5b91d7104865ae6af67d192acc1f
Source dataset
uspto-grants-2001_04
Patent number
US06222062B1

Reaction notes

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