Thionyl Chloride → 6-Methoxy-1-naphthoyl chloride

HRID 333631

Reaction equation

HRID 333631 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([C:13]([OH:15])=O)=[CH:8][CH:7]=[CH:6]2.S(Cl)([Cl:18])=O>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([C:13]([Cl:18])=[O:15])=[CH:8][CH:7]=[CH:6]2

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 44137086-Methoxy-1-naphthoic acid

Product 1

HCID 575166936-Methoxy-1-naphthoyl chloride

Procedure

Under an argon atmosphere, 6-methoxy-1-naphthoic acid (synthesized by the process of J. D. Moseley and J. P. Gilday, Tetrahedron, 62, 4690-4697 (2006)) (1.20 g, 5.93 mmol) was dissolved in thionyl chloride (5.00 mL, 68.8 mmol) and the solution was heated to reflux for 3 hours. After cooling to room temperature, the mixture was concentrated under reduced pressure to give the crude product of 6-methoxy-1-naphthoyl chloride (22) as a colorless oil. The product was used in the following reaction without further purification.

Workup

  1. temperaturethe solution was heated
  2. temperatureto reflux for 3 hours
  3. concentrationthe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-832c16d399ee4da6b25e9bc7fd078d58
Source dataset
uspto-grants-2014_11
Patent number
US08883432B2

Linked notes

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