HCID 18918301, compound → Ethyl 3-(4-hydroxyphenoxy)butyrate

HRID 1291907Notes

Reaction equation

HRID 1291907 reaction equation
C([O:8][C:9]1[CH:23]=[CH:22][C:12]([O:13][CH:14]([CH3:21])[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:11][CH:10]=1)C1C=CC=CC=1.[H][H]>C(O)C.[Pd]>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([O:13][CH:14]([CH3:21])[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:22][CH:23]=1

Participants

5

Reactant 2

HCID 18918301HCID 18918301, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18918541Ethyl 3-(4-hydroxyphenoxy)butyrateYield 93.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of the product of step (i) (4.5 g) in absolute ethanol (200 ml) was added 10% palladium-on-charcoal catalyst (1.2 g) and the resulting suspension hydrogenated at ambient temperature and pressure until uptake of hydrogen ceased. The catalyst was removed by filtration through celite and the filtrate was concentrated in vacuo to give ethyl 3-(4-hydroxyphenoxy)butyrate as a low-melting crystalline solid (3.0 g) NMR (d6DMSO) : δ 1.25 (3H,t); 1.8-2.0 (2H,m); 2.5 (2H,t); 3.9 (2H,t); 4.1 (2H,q); 6.7 (4H,m); 8.8 (1H,br.s); m/e 224 (M)+.

Workup

  1. customhydrogenated at ambient temperature
  2. customThe catalyst was removed by filtration through celite
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-becdf545e38b4f2b84bb96fd70492271
Source dataset
uspto-grants-1998_05
Patent number
US05753659

Reaction notes

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