3-Hydroxy-2-naphthoic acid → 3-Hydroxynaphthalene-2-carbonyl chloride

HRID 1292492Notes

Reaction equation

HRID 1292492 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.S(Cl)([Cl:17])=O>C1(C)C(C)=CC=CC=1>[OH:1][C:2]1[C:3]([C:12]([Cl:17])=[O:14])=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

4

Reactant 2

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

Product 1

HCID 128963863-Hydroxynaphthalene-2-carbonyl chlorideYield 585.5%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent2×

Procedure

494.0 g (2.63 mol) of 3-hydroxy-2-naphthoic acid and 2470.0 g=2872 ml of xylene are initially introduced into a 2 l four-necked flask having an internal thermometer, gas removal tube and stirrer, 6.0 g of N,N'-dimethylformamide are added, 328.0 g=201.1 ml (2.76 mol) of thionyl chloride are metered in at 47°-50°0C. over the course of 1 h and the mixture is subsequently stirred for 3 h until evolution of gas has ended. 3181.8 g of 3-hydroxy-2-naphthoyl chloride are obtained as a clear solution in xylene.

Workup

  1. customan internal thermometer, gas removal tube and stirrer, 6.0 g of N,N'-dimethylformamide
  2. additionare added
  3. customare metered in at 47°

Sources & evidence

ORD record
ord-be749eea4a454b44a46979cac6e2ca33
Source dataset
uspto-grants-1998_05
Patent number
US05756757

Reaction notes

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