Thionyl Chloride → HCID 54277526, compound

HRID 2413248Notes

Reaction equation

HRID 2413248 reaction equation
S(Cl)([Cl:3])=O.[CH3:5][O:6][C:7]([C:9]1[CH:10]=[CH:11][C:12]2[O:16][C:15]([CH2:17]O)=[C:14]([CH3:19])[C:13]=2[CH:20]=1)=[O:8]>N1C=CC=CC=1.C(Cl)(Cl)Cl>[CH3:5][O:6][C:7]([C:9]1[CH:10]=[CH:11][C:12]2[O:16][C:15]([CH2:17][Cl:3])=[C:14]([CH3:19])[C:13]=2[CH:20]=1)=[O:8]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 54506149HCID 54506149, compound

Product 1

HCID 54277526HCID 54277526, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 6212ChloroformSolvent

Procedure

Thionyl chloride (0.25 ml) was added dropwise to a stirred solution of 2-hydroxymethyl-3-methylbenzofuran-5-carboxylic acid methyl ester (0.20 g) and pyridine (2 drops) in chloroform (5 ml). The solution was stirred at room temperature for 30 minutes and then washed successively with water, sodium bicarbonate solution and dried (Na2SO4). Evaporation of the solvent gave crude 2-chloromethyl-3-methylbenzofuran-5-carboxylic acid methyl ester (0.18 g), m.p. 114°-115° which was used directly in the next stage.

Workup

  1. washwashed successively with water, sodium bicarbonate solution
  2. dry with materialdried (Na2SO4)
  3. customEvaporation of the solvent

Sources & evidence

ORD record
ord-10281ea1c21a4fd2bf09eb5ee67f64f1
Source dataset
uspto-grants-1985_01
Patent number
US04496572

Reaction notes

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