HCID 14986288, compound → HCID 15086651, compound

HRID 2108268Notes

Reaction equation

HRID 2108268 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH3:18])[CH:10]=1)=O>[Pd].S(=O)(=O)(O)O.C(O)(=O)C>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH3:18])[CH:10]=1

Participants

5

Reactant 1

HCID 14986288HCID 14986288, compound

Product 1

HCID 15086651HCID 15086651, compoundYield 91.3%

Reagents, catalysts & solvents 3

HCID 1118Sulfuric AcidCatalystHCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 32.9 g of 1-(6-bromo-1-oxohexyl)-3,4-dimethoxybenzene, 3.0 g of 10% palladium on carbon and 5 drops of concentrated sulfuric acid in 200 mL of acetic acid was shaken under hydrogen pressure for 9 hours in a Parr hydrogenator at an initial pressure of 55 psi. The reaction mixture was filtered through Celite and the filtrate was concentrated at reduced pressure. The residue was purified by HPLC using 10% ethyl acetate-hexane to give 28.7 g (91% yield) of 1-(6-bromohexyl)-3,4-dimethoxybenzene as an oil. The nmr spectrum was consistent with the structure and the low resolution mass spectrum showed the molecular ion at m/z 300 (C14H21BrO2).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated at reduced pressure
  3. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-7bf7d15da52d49c6ac524f4a895989e1
Source dataset
uspto-grants-1990_06
Patent number
US04937373

Reaction notes

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