Methacrolein → HCID 69470120, compound

HRID 1180413Notes

Reaction equation

HRID 1180413 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][CH:3]=1.C([Li])CCC.[CH3:14][C:15](=[CH2:18])[CH:16]=[O:17].[NH4+].[Cl-]>C1COCC1>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([CH:16]([OH:17])[C:15]([CH3:18])=[CH2:14])=[CH:3][CH:4]=1

Participants

6

Reactant 4

HCID 6562MethacroleinHCID 78041,4-DibromobenzeneHCID 25517Ammonium ChlorideHCID 178418339Butyllithium

Product 1

HCID 69470120HCID 69470120, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a cold (−78° C.) solution of 1,4-dibromobenzene 1 (42.4 mmol, 10 g) in THF (60 mL) was added butyl lithium(42.4 mmol, 2.5 M in hexane). The mixture was stirred at −78° C. for 1 h. 2-methylpropenal (42.4 mmol, 2.97 g) was added. The mixture was stirred at −78° C. for 1 h. NH4Cl was added. The mixture was extracted with EtOAc. The organic extract was washed with brine, dried and concentrated to an oil. Chromatography (5-15% EtOAc/hexane) gave the desired alcohol.

Workup

  1. stirringThe mixture was stirred at −78° C. for 1 h
  2. extractionThe mixture was extracted with EtOAc
  3. extractionThe organic extract
  4. washwas washed with brine
  5. customdried
  6. concentrationconcentrated to an oil

Sources & evidence

ORD record
ord-1e9e5256e8bf4be7abf7d0bfe371666e
Source dataset
uspto-grants-2007_10
Patent number
US07279478B2

Reaction notes

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