Phenol, 3-(1,1-dimethylethyl)- → HCID 54979430, compound

HRID 348313Notes

Reaction equation

HRID 348313 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([OH:11])[CH:8]=[CH:9][CH:10]=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:7]1[CH:8]=[CH:9][CH:10]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH:6]=1)[CH3:21])[CH3:20]

Participants

6

Reactant 3

HCID 11450Phenol, 3-(1,1-dimethylethyl)-HCID 24758Sodium hydrideHCID 79040Ethyl 2-bromopropionate

Product 1

HCID 54979430HCID 54979430, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-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.

Workup

  1. extractionextracted twice with water and once with brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customto produce a colorless oil

Sources & evidence

ORD record
ord-899c2e1d0e5f43f381a10d40986455a0
Source dataset
uspto-grants-2007_02
Patent number
US07176224B2

Reaction notes

Loading…