Sulfuryl chloride → 2-Chloro-3-hydroxy-5-(3-methoxypropyl)benzaldehyde

HRID 561823Notes

Reaction equation

HRID 561823 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([CH2:10][CH2:11][CH2:12][O:13][CH3:14])[CH:9]=1)[CH:5]=[O:6].S(Cl)([Cl:18])(=O)=O>ClCCl>[Cl:18][C:3]1[C:2]([OH:1])=[CH:9][C:8]([CH2:10][CH2:11][CH2:12][O:13][CH3:14])=[CH:7][C:4]=1[CH:5]=[O:6]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 53429202HCID 53429202, compound

Product 1

HCID 866359212-Chloro-3-hydroxy-5-(3-methoxypropyl)benzaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-hydroxy-5-(3-methoxypropyl)benzaldehyde from the previous step (I eq.) in dichloromethane (0.2 M) was added sulfuryl chloride (1 eq.). The resulting reaction mixture was then stirred at RT for 18 h. The volatiles were removed in vacuo and purification of the crude product thus obtained by way of column chromatography (SiO2, Hex→3:2 (v/v) Hex:EtOAc) afforded the title compound as a yellow oil.

Workup

  1. customThe resulting reaction mixture
  2. customThe volatiles were removed in vacuo and purification of the crude product
  3. customthus obtained by way of column chromatography (SiO2, Hex→3:2 (v/v) Hex:EtOAc)

Sources & evidence

ORD record
ord-d0a826634e2041c2b467da77ad815ef4
Source dataset
uspto-grants-2011_11
Patent number
US08063105B2

Reaction notes

Loading…