Azane;hydrate → Ethyl 4-undecylphenylacetate

HRID 1650812Notes

Reaction equation

HRID 1650812 reaction equation
O[CH:2]([C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:15][CH:14]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[H][H].O.N>C(O)(=O)C.[Pd]>[CH2:2]([C:13]1[CH:14]=[CH:15][C:16]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:17][CH:18]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

6

Reactant 3

HCID 12896473Azane;hydrateHCID 23052531Ethyl 4-(1-hydroxyundecyl)phenylacetateHCID 178418361HCID 178418361, compound

Product 1

HCID 23052528Ethyl 4-undecylphenylacetateYield 88.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

To the solution of ethyl 4-(1-hydroxyundecyl)-phenylacetate (9.7 g, 0.029 mol) in acetic acid (50 ml) was added 10%-palladium on carbon. The reaction mixture was stirred for 18 hours under 1 atmospheric pressure of hydrogen and then poured onto the mixture of concentrated ammonia water (100 ml) and ice (100 g). The resultant precipitate was extracted with ethyl acetate. The organic layer was washed with water, dried and concentrated under reduced pressure to obtain ethyl 4-undecylphenylacetate (3-w, 8.2 g, 88%) as an oil.

Workup

  1. extractionThe resultant precipitate was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. customdried
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1bb7cc8305934ca89276795fecb0cf15
Source dataset
uspto-grants-1990_05
Patent number
US04925868

Reaction notes

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