4-Methoxy-3-(4-methoxy-2-butenyl)-bromobenzene → 4-Bromo-1-methoxy-2-(4-methoxybutyl)benzene

HRID 744853Notes

Reaction equation

HRID 744853 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([Br:9])=[CH:5][C:4]=1[CH2:10][CH:11]=[CH:12][CH2:13][O:14][CH3:15]>O1CCCC1.[Pt]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([Br:9])=[CH:5][C:4]=1[CH2:10][CH2:11][CH2:12][CH2:13][O:14][CH3:15]

Participants

4

Reactant 1

HCID 541427744-Methoxy-3-(4-methoxy-2-butenyl)-bromobenzene

Product 1

HCID 214586274-Bromo-1-methoxy-2-(4-methoxybutyl)benzene

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 50 g of 4-methoxy-3-(4-methoxy-2-butenyl)-bromobenzene in 700 ml of tetrahydrofuran is hydrogenated for 2 hours under normal pressure and at room temperature in the presence of 2.5 g of 5% Pt/C. The reaction mixture is filtered. The filtrate is concentrated by evaporation. The evaporation residue obtained from the filtrate is purified by FC (1.6 kg of silica gel, hexane/ethyl acetate=20:1). Distillation under a high vacuum yields the title compound: Rt (hexane/ethyl acetate=10:1)=0.38; HPLC Rt =19.92 minutes; FAB-MS (M+H)+ =273.

Workup

  1. filtrationThe reaction mixture is filtered
  2. concentrationThe filtrate is concentrated by evaporation
  3. customThe evaporation residue obtained from the filtrate
  4. customis purified by FC (1.6 kg of silica gel, hexane/ethyl acetate=20:1)
  5. distillationDistillation under a high vacuum

Sources & evidence

ORD record
ord-2df88ef682954b54a4a4e698c87f16a0
Source dataset
uspto-grants-1996_09
Patent number
US05559111

Reaction notes

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