Chlorine → HCID 14986399, compound

HRID 1613076Notes

Reaction equation

HRID 1613076 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][OH:17])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[Cl:18]Cl>C(Cl)Cl>[Cl:18][C:6]1[C:5]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][OH:17])=[CH:4][C:3]([O:2][CH3:1])=[C:8]([O:9][CH3:10])[CH:7]=1

Participants

4

Reactant 2

HCID 24526ChlorineHCID 14986398HCID 14986398, compound

Product 1

HCID 14986399HCID 14986399, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 1.40 g of 6-(3,4-dimethoxyphenyl)hexan-1-ol in 25 mL of methylene chloride cooled in a ethanol-dry ice bath was added 4.6 mL of 1.35M chlorine in methylene chloride. The reaction mixture was kept at -75° for 1.5 hours, at -18° for 16 hours and then at 0° for 24 hours. After concentration under reduced pressure, the crude product was purified by HPLC to give 6-(6-chloro-3,4-dimethoxyphenyl)hexan-1-ol as an oil. The nmr spectrum was consistent with the structure and the mass spectrum gave a molecular ion at m/z 272 (C14H21ClO3).

Workup

  1. waitat 0° for 24 hours
  2. concentrationAfter concentration under reduced pressure
  3. customthe crude product was purified by HPLC

Sources & evidence

ORD record
ord-c6b9116e8a0c4c62b3568585d814c7d0
Source dataset
uspto-grants-1993_03
Patent number
US05191108

Reaction notes

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