Naphthalene → HCID 22987106, compound

HRID 987879Notes

Reaction equation

HRID 987879 reaction equation
[C:1]([C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:14]([OH:16])=[O:15])[CH:10]=2)[CH:5]=1)([OH:3])=[O:2].C1C2C(=CC=CC=2)C=CC=1.S(Cl)([Cl:29])=O>>[C:14]([C:9]1[CH:8]=[CH:7][C:6]2[C:11](=[CH:12][CH:13]=[C:4]([C:1]([OH:3])=[O:2])[CH:5]=2)[C:10]=1[Cl:29])([OH:16])=[O:15]

Participants

4

Reactant 3

HCID 931NaphthaleneHCID 143572,6-Naphthalenedicarboxylic acidHCID 24386Thionyl Chloride2×

Product 1

HCID 22987106HCID 22987106, compound

Conditions

Temperature
80 °C

Procedure

2,6-Dicarboxynaphthalene having carboxyl groups bonded to a naphthalene nucleus, designated compound A, is chosen as a starting compound. Two moles of thionyl chloride is added to one mole of compound A, and the mixture is heated to about 75 to 90° C., preferably about 80° C., with stirring in a nitrogen atmosphere. Then the stirring force is diminished, and the reaction mixture is refluxed for about 6 to 18 hours, desirably about 10 to 12 hours. The bath temperature is set at about 90 to 100° C., at which unreacted thionyl chloride is removed by evaporation over about 2 hours to obtain 2,6-dicarboxychloronaphthalene, designated compound B.

Workup

  1. temperaturethe reaction mixture is refluxed for about 6 to 18 hours, desirably about 10 to 12 hours
  2. customis removed by evaporation over about 2 hours

Sources & evidence

ORD record
ord-474bfa7fc8df42e2ad02989461ee8218
Source dataset
uspto-grants-2003_10
Patent number
US06632916B2

Reaction notes

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