(3-Bromopropyl)benzene → HCID 54295172, compound

HRID 1598627Notes

Reaction equation

HRID 1598627 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Mg].[CH3:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][C:20]=1[O:21][CH3:22])[CH:16]=[O:17]>C1COCC1>[CH3:12][C:13]1[CH:14]=[C:15]([CH:16]([OH:17])[CH2:9][CH2:8][CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:18]=[CH:19][C:20]=1[O:21][CH3:22]

Participants

5

Reactant 3

HCID 12503(3-Bromopropyl)benzeneHCID 1229363-Methyl-4-anisaldehydeHCID 5462224Magnesium

Product 1

HCID 54295172HCID 54295172, compoundYield 58.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3-Phenyl-1-1-propyl magnesium bromide was prepared from the reaction of 3-phenyl-1-bromopropane (8.0 mL. 52.6 mmol) and magnesium turnings (1.40 g, 57.6 mmol) in THF. This solution was added dropwise to an ice-water cooled solution of 3-methyl-para-anisaldehyde (7.70 mL. 52.6 mmol) in THF. The resulting reaction was allowed to warm to room temperature, and after 1h was partitioned between aqueous ammonium chloride and ether. The organic phase was dried over magnesium sulfate, concentrated, and purified by chromatography over silica gel eluted with 15% ethyl acetate in hexanes to afford 8.35 g of 2-methyl-4-(1-hydroxy-4-phenyl-1-butyl) anisole as a clear oil.

Workup

  1. customThe resulting reaction
  2. customafter 1h was partitioned between aqueous ammonium chloride and ether
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. concentrationconcentrated
  5. custompurified by chromatography over silica gel
  6. washeluted with 15% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-297ac297e6da46b4adf43effecea7b15
Source dataset
uspto-grants-1998_04
Patent number
US05739140

Reaction notes

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