1-Iodopropane → 2-Hydroxy-6-methyl-4-propoxy-benzoic acid methyl ester

HRID 644003Notes

Reaction equation

HRID 644003 reaction equation
I[CH2:2][CH2:3][CH3:4].[C:5]([O:16][CH3:17])(=[O:15])[C:6]1[C:7](=[CH:9][C:10](=[CH:12][C:13]=1[CH3:14])[OH:11])[OH:8].C(=O)(O)[O-].[Na+]>CN(C=O)C>[CH3:17][O:16][C:5](=[O:15])[C:6]1[C:13]([CH3:14])=[CH:12][C:10]([O:11][CH2:2][CH2:3][CH3:4])=[CH:9][C:7]=1[OH:8]

Participants

5

Reactant 3

HCID 336431-IodopropaneHCID 76658Methyl OrsellinateHCID 516892Sodium Bicarbonate

Product 1

HCID 685799482-Hydroxy-6-methyl-4-propoxy-benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 1-iodopropane (1.87 g, 10.98 mmol), methyl orsellinate (2.0 g, 10.98 mmol), and sodium bicarbonate (1.84 g, 21.96 mmol) in DMF is stirred at 60° C. overnight. The mixture is cooled and partitioned between EtOAc and water. The EtOAc layer is washed with brine, dried over magnesium sulfate, and concentrated to give the crude product. Purification by silica gel chromatography using 2% EtOAc in hexane as the eluent gives 2-hydroxy-6-methyl-4-propoxy-benzoic acid methyl ester.

Workup

  1. temperatureThe mixture is cooled
  2. custompartitioned between EtOAc and water
  3. washThe EtOAc layer is washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customto give the crude product
  7. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-bd6f25c7275b4ab49fe7c441a64fcaa5
Source dataset
uspto-grants-2010_04
Patent number
US07700637B2

Reaction notes

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