Thionyl Chloride → 3-(Benzyloxy)-5-methoxybenzoyl chloride

HRID 38657

Reaction equation

HRID 38657 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]=[C:16]([O:18][CH3:19])[CH:17]=1)[C:12](O)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:22])=O>C1(C)C=CC=CC=1.CN(C)C=O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]=[C:16]([O:18][CH3:19])[CH:17]=1)[C:12]([Cl:22])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 126587813-(Benzyloxy)-5-methoxybenzoic acid

Product 1

HCID 126587833-(Benzyloxy)-5-methoxybenzoyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 1140TolueneSolvent

Procedure

3-(Benzyloxy)-5-methoxybenzoic acid (162) (2.57 g, 0.01 mmol) and thionyl chloride (4.80 g, 0.04 mmol) were suspended in 200 mL of dry toluene. The reaction mixture was stirred for 30 min and then dimethyl formamide (3 drops) was added. The mixture was stirred for 24 h and then evaporated to dryness. The residue was directly used for the next step without further purification.

Workup

  1. stirringThe mixture was stirred for 24 h
  2. customevaporated to dryness
  3. customThe residue was directly used for the next step without further purification

Sources & evidence

ORD record
ord-3c9d93c5e3544b2ab3e9203f54d79d47
Source dataset
uspto-grants-2013_09
Patent number
US08524740B2

Linked notes

Loading…