Water → 5-Chloro-2-hydroxy-3-methoxybenzaldehyde

HRID 892173

Reaction equation

HRID 892173 reaction equation
S(Cl)([Cl:4])(=O)=O.[O:6]=[CH:7][C:8]1[CH:16]=[CH:15][CH:14]=[C:11]([O:12][CH3:13])[C:9]=1[OH:10].O>C1(C)C=CC=CC=1>[Cl:4][C:15]1[CH:14]=[C:11]([O:12][CH3:13])[C:9]([OH:10])=[C:8]([CH:16]=1)[CH:7]=[O:6]

Participants

5

Reactant 3

HCID 962WaterHCID 8991o-VanillinHCID 24648Sulfuryl chloride

Product 1

HCID 51510865-Chloro-2-hydroxy-3-methoxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of sulfuryl chloride (15 mL, 190 mmol) in toluene (20 mL) is added dropwise over 1.5 h to a solution of o-vanillin (25.0 g, 164 mmol) in toluene (90 mL) and the reaction is then stirred 16 h. Water (30 mL) is added over 10 minutes with ice-bath cooling. The solid is filtered, washed with water and dried to provide the title compound. MS (EI) 186 (M)+.

Workup

  1. temperaturecooling
  2. filtrationThe solid is filtered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-17aa28f080b149d99a1ef1821d5e4992
Source dataset
uspto-grants-2006_02
Patent number
US07005440B1

Linked notes

Loading…