Methyl iodide → Methyl 3-(1-hydroxybut-3-en-1-yl)-4-methylbenzoate

HRID 1487828Notes

Reaction equation

HRID 1487828 reaction equation
[OH:1][CH:2]([C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][C:14]=1[CH3:15])[C:9]([OH:11])=[O:10])[CH2:3][CH:4]=[CH2:5].[C:16](=O)(O)[O-].[Na+].CI>CN(C)C=O>[OH:1][CH:2]([C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][C:14]=1[CH3:15])[C:9]([O:11][CH3:16])=[O:10])[CH2:3][CH:4]=[CH2:5]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 516892Sodium BicarbonateHCID 900666783-(1-Hydroxy-3-buten-1-yl)-4-methylbenzoic acid2×

Product 1

HCID 90066664Methyl 3-(1-hydroxybut-3-en-1-yl)-4-methylbenzoateYield 53.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

Into a 100-mL round-bottom flask, was added a solution of 3-(1-hydroxybut-3-en-1-yl)-4-methylbenzoic acid (compound 4.2, 1.4 g, 6.79 mmol) in N,N-dimethylformamide (20 mL). Sodium bicarbonate (1.14 g, 13.6 mmol) and methyl iodide (0.847 mL, 13.6 mmol) were added and the resulting mixture was stirred overnight at 25° C. The reaction was quenched with saturated aqueous Na2S2O3 (50 mL) and diluted with EtOAc (150 mL). The organic layer was washed with brine (3×50 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography with ethyl acetate/petroleum ether (1:3) as the eluent to yield the title compound as a light yellow oil (800 mg, 53%).

Workup

  1. customThe reaction was quenched with saturated aqueous Na2S2O3 (50 mL)
  2. additiondiluted with EtOAc (150 mL)
  3. washThe organic layer was washed with brine (3×50 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography with ethyl acetate/petroleum ether (1:3) as the eluent

Sources & evidence

ORD record
ord-472343f80cae4046bfd17260191c4e71
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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