4-tert-Butylphenol → Ethyl 2-(4-tert-butylphenoxy)propanoate

HRID 348301Notes

Reaction equation

HRID 348301 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Br[CH:15]([CH3:21])[C:16]([O:18][CH2:19][CH3:20])=[O:17]>CN(C=O)C.C(OCC)(=O)C>[CH2:19]([O:18][C:16](=[O:17])[CH:15]([O:11][C:8]1[CH:7]=[CH:6][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:10][CH:9]=1)[CH3:21])[CH3:20]

Participants

6

Reactant 3

HCID 73934-tert-ButylphenolHCID 24758Sodium hydrideHCID 79040Ethyl 2-bromopropionate

Product 1

HCID 3023318Ethyl 2-(4-tert-butylphenoxy)propanoateYield 100%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-tert-butylphenol (7.52 g, 50 mmol) in anhydrous DMF (40 mL) was added dropwise to NaH (2.2 g, 55 mmol, 60% w/w in mineral oil) at 0° C. under an atmosphere of nitrogen. After five min, ethyl 2-bromopropionate (6.49 mL, 50 mmol, d=1.394) was added rapidly dropwise and the resultant mixture was allowed to stir for 18 h, gradually warming to ambient temperature. The reaction mixture was diluted with ethyl acetate (300 mL) and extracted twice with water and once with brine. The organic layer was dried over Na2SO4 and concentrated in vacuo to produce a colorless oil (12.5 g, 100%) 1H NMR (300 MHz, CDCl3): δ 7.28 (d, 2H, J=5.5), 6.80 (d, 2H, J=5.5), 4.70 (q, 1H, J=6.6), 4.22 (q, 2H, J=7.1), 1.59 (d, 3H, J=6.6), 1.28 (s, 9H), 1.25 (t, 3H, J=7.1). MS [EI+] 251 (M+H)+, 268 (M+NH4)+.

Workup

  1. extractionextracted twice with water and once with brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b3ef37844ef2488086f61b09b05df4e6
Source dataset
uspto-grants-2007_02
Patent number
US07176224B2

Reaction notes

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