Hydrochloric Acid → HCID 86609983, compound

HRID 1176219Notes

Reaction equation

HRID 1176219 reaction equation
[OH:1][C:2]1[C:9]([OH:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[H-].[Na+].Cl[CH2:14][CH2:15][CH2:16][O:17][CH3:18].[I-].[Na+].Cl>CS(C)=O>[OH:1][C:2]1[C:9]([O:10][CH2:14][CH2:15][CH2:16][O:17][CH3:18])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 905792,3-DihydroxybenzaldehydeHCID 1189271-Chloro-3-methoxypropane

Product 1

HCID 86609983HCID 86609983, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent3×

Procedure

A solution of 5.00 g of 2,3-dihydroxybenzaldehyde in 10 ml of dimethyl sulphoxide is added dropwise at room temperature to the suspension of 3.77 g of sodium hydride dispersion (55%) in 28 ml of dimethyl sulphoxide. The reaction mixture is stirred over 1 hour and then admixed with a solution of 3.81 g of 1-chloro-3-methoxypropane in 2 ml of dimethyl sulphoxide. After 2 hours, 0.50 g of sodium iodide is added. After 16 hours, the reaction mixture is poured onto water, acidified to pH 2 with 4N HCl and extracted with dichloromethane (7×). The combined organic phases are washed with 0.5N HCl (2×), dried over sodium sulphate and concentrated by evaporation. The title compound is obtained as a yellow oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.23 (95:5 dichloromethane-methanol); Rt=3.60.

Workup

  1. waitAfter 2 hours
  2. waitAfter 16 hours
  3. additionthe reaction mixture is poured onto water
  4. extractionextracted with dichloromethane (7×)
  5. washThe combined organic phases are washed with 0.5N HCl (2×)
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-41cb095af0fa4087a56ab88d204f58a9
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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