Dimethylformamide → 3-Hydroxynaphthalene-2-carbonyl chloride

HRID 1292495Notes

Reaction equation

HRID 1292495 reaction equation
[OH:1][C:2]1[C:3]([C:12]([OH:14])=O)=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.CN(C=O)C.S(Cl)([Cl:22])=O>ClC1C=CC=CC=1>[OH:1][C:2]1[C:3]([C:12]([Cl:22])=[O:14])=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 71043-Hydroxy-2-naphthoic acidHCID 24386Thionyl Chloride

Product 1

HCID 128963863-Hydroxynaphthalene-2-carbonyl chlorideYield 723%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
40 °C

Procedure

99.0 g (0.52 mol) of 3-hydroxy-2-naphthoic acid and 1 ml of N,N'-dimethylformamide are initially introduced into 600 ml of chlorobenzene and 68.5 g=42 ml (0.58 mol) of thionyl chloride are added at 40° C. The mixture is subsequently stirred at 40° C. for 1.5 h and excess thionyl chloride is then distilled off in vacuo. 776.8 g of 3-hydroxy-2-naphthoyl chloride are obtained as a clear solution in chlorobenzene.

Workup

  1. additionare added at 40° C
  2. distillationexcess thionyl chloride is then distilled off in vacuo

Sources & evidence

ORD record
ord-010f57394163451cbeb2f2c469a5bced
Source dataset
uspto-grants-1998_05
Patent number
US05756757

Reaction notes

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