2-Methyl-2-butene → 4-Methoxynaphthalene-1-carboxylic acid

HRID 55930Notes

Reaction equation

HRID 55930 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([CH:13]=[O:14])=[CH:5][CH:4]=1.CC(=CC)C.Cl([O-])=[O:21].[Na+].P([O-])(O)(O)=O.[Na+]>C(O)(C)(C)C.O>[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C:13]([OH:21])=[O:14])=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 105532-Methyl-2-buteneHCID 852174-Methoxy-1-naphthaldehydeHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphate

Product 1

HCID 7653804-Methoxynaphthalene-1-carboxylic acidYield 55%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

4-Methoxy-1-naphthaldehyde (10 g, 53.72 mmol) was dissolved in t-butanol (75 ml) and 2-methyl-2-butene (35 ml) was added at room temperature. A solution of sodium chlorite (7.99 g, 70.63 mmol) and sodium dihydrogen orthophosphate (9.15 g, 76.27 mmol) in water (50 ml) was added dropwise. The reaction mixture was stirred at room temperature overnight. The reaction mixture was concentrated in vacuo and the residue was washed with a solution of 2MHCl (100 ml) and the solid was filtered and washed with dichloromethane (100 ml) and water (100 ml) and dried in vacuo. The solid was recrystallised from methanol to give 5.95 g (55%) of 4-methoxy-1-naphthoic acid as cream crystals.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. washthe residue was washed with a solution of 2MHCl (100 ml)
  3. filtrationthe solid was filtered
  4. washwashed with dichloromethane (100 ml) and water (100 ml)
  5. customdried in vacuo
  6. customThe solid was recrystallised from methanol

Sources & evidence

ORD record
ord-caa467221c7e4d0abe131895b0dba29a
Source dataset
uspto-grants-2016_09
Patent number
US09434687B2

Reaction notes

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