HCID 68774438, compound → Benzoic acid, 2-hydroxy-, (3Z)-1-methyl-3-hexen-1-yl ester

HRID 1175651Notes

Reaction equation

HRID 1175651 reaction equation
[C:1]([O:10][CH:11]([CH2:13][C:14]#[C:15][CH2:16][CH3:17])[CH3:12])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4]>[Pd].C(O)C>[C:1]([O:10][CH:11]([CH2:13]/[CH:14]=[CH:15]\[CH2:16][CH3:17])[CH3:12])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4]

Participants

4

Reactant 1

HCID 68774438HCID 68774438, compound

Product 1

HCID 67480918Benzoic acid, 2-hydroxy-, (3Z)-1-methyl-3-hexen-1-yl esterYield 92.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

4-Heptyn-2-yl salicylate (24.6 g; 0.1 mol) dissolved in 30 ml abs. ethanol are stirred over palladium on bariumsulfate (0.4 g; 0.02 mol) and under hydrogen for 3 hours. Filtration over Celite and evaporation of the ethanol under reduced pressure gives 26.2 g crude product which is distilled over a Vigreux column giving 23.5 g (96%) of a slightly yellowish oil at 98° C./0.1 Torr (0.133 mbar). Redistillation under the same conditions gives 21.6 g (88%) of colorless (Z)-4-hepten-2-yl salicylate.

Workup

  1. filtrationFiltration
  2. customover Celite and evaporation of the ethanol under reduced pressure
  3. customgives 26.2 g crude product which
  4. distillationis distilled over a Vigreux column
  5. customgiving 23.5 g (96%) of a slightly yellowish oil at 98° C./0.1 Torr (0.133 mbar)
  6. distillationRedistillation under the same conditions

Sources & evidence

ORD record
ord-952981e168a443e2b1b9cc3df1cf7360
Source dataset
uspto-grants-2010_11
Patent number
US07842660B2

Reaction notes

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