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

HRID 725660Notes

Reaction equation

HRID 725660 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 PC (1.6 kg of silica gel, hexane/ethyl acetate=20:1). Distillation under a high vacuum yields the title compound: Rf (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 PC (1.6 kg of silica gel, hexane/ethyl acetate=20:1)
  5. distillationDistillation under a high vacuum

Sources & evidence

ORD record
ord-86264525305646d6ace8dd7ea984aeb3
Source dataset
uspto-grants-1998_01
Patent number
US05705658

Reaction notes

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