Hydrochloric Acid → Methyl 4-methylnaphthalene-1-carboxylate

HRID 11857Notes

Reaction equation

HRID 11857 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]([OH:14])=[O:13])=[CH:4][CH:3]=1.Cl.[CH3:16]O>>[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]([O:14][CH3:16])=[O:13])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 30142854-Methyl-1-naphthalenecarboxylic acid

Product 1

HCID 21973653Methyl 4-methylnaphthalene-1-carboxylate

Procedure

Commercially available 4-methyl-1-naphthalenecarboxylic acid (250.6 mg) was dissolved in methanol (7.5 ml). Hydrogen chloride gas was blown into the solution for five minutes while cooling with ice. Then, the mixture was stirred for 19 hours at room temperature and the solvent was removed by distillation. The residue was dissolved in chloroform, washed with 1 mol/l aqueous solution of sodium hydroxide, and dried over anhydrous sodium sulfate. The solvent was removed by distillation. The residue was dried under reduced pressure to obtain the target compound (269.9 mg) as colorless oil.

Workup

  1. temperaturewhile cooling with ice
  2. customthe solvent was removed by distillation
  3. dissolutionThe residue was dissolved in chloroform
  4. washwashed with 1 mol/l aqueous solution of sodium hydroxide
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was removed by distillation
  7. customThe residue was dried under reduced pressure

Sources & evidence

ORD record
ord-b8d808e82a4642758ddd699886c22acc
Source dataset
uspto-grants-2006_08
Patent number
US07098215B2

Reaction notes

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