Methyl iodide → HCID 23445614, compound

HRID 1280885Notes

Reaction equation

HRID 1280885 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([CH3:11])[C:9]=1[OH:10])[CH:5]=[O:6].[H-].[Na+].I[CH3:15]>C1COCC1>[I:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([CH3:11])[C:9]=1[O:10][CH3:15])[CH:5]=[O:6]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 23445631HCID 23445631, compound

Product 1

HCID 23445614HCID 23445614, compoundYield 60.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

At 5° C., to a stirred solution of 3-iodo-4-hydroxy-5-methylbenzaldehyde (3.53 g, 13.5 mmol) in THF (67.4 mL) was added 60% sodium hydride/mineral oil (0.701 g, 17.5 mmol). After 0.5 h, to the reaction was added dropwise iodomethane (1.34 mL, 21.6 mmol). After 2 h, the reaction was heated at 60° C. After 3 days, the reaction was cooled to ambient temperature, quenched with H2O (100 mL) and extracted with ether. The ethereal extracts were washed with 1N NaOH (3×), with brine (3×), dried (ACO3) and concentrated. Purification on Biotage KP-Sil eluting with 15% acetone/hexane gave 2.24 g (60%) of the title compound. 1H NMR (DMSO-d6) δ 2.37 (s, 3H), 3.77 (s, 3H), 7.78 (s, 1H), 8.17 (s, 1H), 9.86 (s, 1H).

Workup

  1. waitAfter 2 h
  2. waitAfter 3 days
  3. temperaturethe reaction was cooled to ambient temperature
  4. customquenched with H2O (100 mL)
  5. extractionextracted with ether
  6. washThe ethereal extracts were washed with 1N NaOH (3×), with brine (3×)
  7. customdried (ACO3)
  8. concentrationconcentrated
  9. customPurification on Biotage KP-Sil
  10. washeluting with 15% acetone/hexane

Sources & evidence

ORD record
ord-08679d6b66f94bf1a29c61ede04b1133
Source dataset
uspto-grants-2002_09
Patent number
US06451845B1

Reaction notes

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