Acetone → Methyl 3-methoxy-4-iodo-2-naphthoate

HRID 1355376Notes

Reaction equation

HRID 1355376 reaction equation
[OH:1][C:2]1[C:3]([C:13]([OH:15])=O)=[CH:4][C:5]2[C:10]([C:11]=1[I:12])=[CH:9][CH:8]=[CH:7][CH:6]=2.S([O:21][CH3:22])(OC)(=O)=O.[C:23](=O)([O-])[O-].[K+].[K+].CC(C)=O>C(N(CC)CC)C>[CH3:23][O:1][C:2]1[C:3]([C:13]([O:21][CH3:22])=[O:15])=[CH:4][C:5]2[C:10]([C:11]=1[I:12])=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

6

Reactant 4

HCID 180AcetoneHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 2422513-Hydroxy-4-iodonaphthalene-2-carboxylic acid

Product 1

HCID 11110626Methyl 3-methoxy-4-iodo-2-naphthoateYield 63.5%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A solution of 3-hydroxy-4-iodo-2-naphthoic acid (8.0 g), dimethyl sulfate (8.03 g), powdered potassium carbonate (8.80 g), and dry acetone (150 mL) was heated under reflux for 18 h. The solution was cooled to room temperature, triethylamine (15 mL) was added, and stirring continued for 30 min. The solution was filtered through a pad of Diatomaceous earth and washed with dry acetone (50 mL). The filtrate was concentrated to a yellow oil, diluted with EtOAc, and washed successively with 1N HCl (100 mL), saturated aqueous sodium bicarbonate (100 mL), and brine (100 mL). The organic phase was dried (sodium sulfate), filtered, concentrated, and purified by chromatography (0-10% EtOAc in hexanes) to afford the product as a yellow oil (5.53 g). 1H NMR (DMSO-d6) δ8.47 (s, 1H), 8.09 (m, 2H), 7.74 (m, 1H), 7.61 (m, 1H), 3.94 (s, 3H), 3.87 (s, 3H).

Workup

  1. temperatureunder reflux for 18 h
  2. filtrationThe solution was filtered through a pad of Diatomaceous earth
  3. washwashed with dry acetone (50 mL)
  4. concentrationThe filtrate was concentrated to a yellow oil
  5. additiondiluted with EtOAc
  6. washwashed successively with 1N HCl (100 mL), saturated aqueous sodium bicarbonate (100 mL), and brine (100 mL)
  7. dry with materialThe organic phase was dried (sodium sulfate)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. custompurified by chromatography (0-10% EtOAc in hexanes)

Sources & evidence

ORD record
ord-bdc8acd01a2c455eaab1d79dbc5f3a37
Source dataset
uspto-grants-2003_07
Patent number
US06586432B2

Reaction notes

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