Iodoethane → Methyl 5-ethoxy-2-methylbenzoate

HRID 577593Notes

Reaction equation

HRID 577593 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[CH2:13](I)[CH3:14].C([O-])([O-])=O.[K+].[K+]>CC#N.CCOC(C)=O.O>[CH2:13]([O:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8])[CH3:14]

Participants

7

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 13929055Methyl 5-hydroxy-2-methylbenzoate

Product 1

HCID 86723821Methyl 5-ethoxy-2-methylbenzoateYield 99.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of methyl 5-hydroxy-2-methylbenzoate (134a, 0.600 g, 3.63 mmol) and ethyl iodide (1.13 g, 7.26 mmol) in CH3CN (10 mL) was added K2CO3 (1.00 g, 7.26 mmol) at room temperature. The resulting mixture was heated at 100° C. for 12 hours. The reaction mixture was diluted with EtOAc (25 mL) and H2O (10 mL). The organic layer was separated and washed with NaOH (2 N, 5 mL), H2O (5 mL) and brine (5 mL), dried over Na2SO4 and concentrated under vacuum to give methyl 5-ethoxy-2-methylbenzoate (134b, 0.7 g, 99%) as yellow liquid.

Workup

  1. customThe organic layer was separated
  2. washwashed with NaOH (2 N, 5 mL), H2O (5 mL) and brine (5 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-65efb1814b5f47e384c1a73536e2a59a
Source dataset
uspto-grants-2015_05
Patent number
US09040515B2

Reaction notes

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