2-Naphthoic acid → 2-Naphthoyl chloride

HRID 645942Notes

Reaction equation

HRID 645942 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([OH:13])=O.O=S(Cl)[Cl:16]>>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([Cl:16])=[O:13]

Participants

3

Reactant 2

HCID 71232-Naphthoic acidHCID 24386Thionyl Chloride

Product 1

HCID 752462-Naphthoyl chlorideYield 100%

Procedure

A 100 mL round bottom flask was charged with 2-naphthoic acid (2 g, 11.6 mmol) and SOCl2 (15 mL). The solution was refluxed for 4 hours and then concentrated to yield a yellow solid which was used without further purification (2.21 g, 100% yield); 1H NMR (CDCl3) δ 8.76 (s, 1H, ArH), 8.04 (2H, ArH), 7.93 (d, 2H, ArH, J=8.9 Hz), 7.66 (m, 2H, ArH).

Workup

  1. temperatureThe solution was refluxed for 4 hours
  2. concentrationconcentrated
  3. customto yield a yellow solid which
  4. customwas used without further purification (2.21 g, 100% yield)

Sources & evidence

ORD record
ord-f7c431432b364c8bb1c5dcb21ea2f5ef
Source dataset
uspto-grants-2010_04
Patent number
US07705022B2

Reaction notes

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