Water → Methyl 6-chloro-2-naphthoate

HRID 973294Notes

Reaction equation

HRID 973294 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([OH:14])=[O:13])[CH:6]=[CH:5]2.S(=O)(=O)(O)O.O.[CH3:21]COCC>CO>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([O:14][CH3:21])=[O:13])[CH:6]=[CH:5]2

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 3283Diethyl EtherHCID 132883276-Chloronaphthalene-2-carboxylic acid

Product 1

HCID 13384252Methyl 6-chloro-2-naphthoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of the 6-chloro-2-naphthoic acid (41.2 g.) in a mixture of methanol (500 ml.) and concentrated sulphuric acid (50 ml.) is heated under reflux for 3 hours, stored at ambient temperature for 3 days, then warmed until a solution is obtained. Water (2 l.) and ether (1 l.) are added. The ethereal layer is separated, and is washed in turn with water, N-aqueous sodium hydroxide, and water, dried with magnesium sulphate, and evaporated to give methyl 6-chloro-2-naphthoate (38.8 g.) m.p. 97°-98° C., which may be further purified by recrystallisation from light petroleum (b.p. 40°-60° C.) to give material of m.p. 100°-101° C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 3 hours
  3. temperaturewarmed until a solution
  4. customis obtained
  5. customThe ethereal layer is separated
  6. washis washed in turn with water, N-aqueous sodium hydroxide, and water
  7. dry with materialdried with magnesium sulphate
  8. customevaporated

Sources & evidence

ORD record
ord-29a4bf438c274156870771b3fa8ef13a
Source dataset
uspto-grants-1977_10
Patent number
US04055595

Reaction notes

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