Sulfuryl chloride → 2-Chloro-3-hydroxy-5-(3-methoxypropyl)benzaldehyde
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
Product 1
Reagents, catalysts & solvents 1
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
- customThe resulting reaction mixture
- customThe volatiles were removed in vacuo and purification of the crude product
- 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
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