Methyl iodide → Methyl 4-methylnaphthalene-1-carboxylate

HRID 1950718Notes

Reaction equation

HRID 1950718 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]([OH:14])=[O:13])=[CH:4][CH:3]=1.[C:15](=O)([O-])[O-].[K+].[K+].CI.CCOC(C)=O>CN(C=O)C.CCCCCC>[CH3:15][O:13][C:12]([C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([CH3:1])=[CH:3][CH:4]=1)=[O:14]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 30142854-Methyl-1-naphthalenecarboxylic acid

Product 1

HCID 21973653Methyl 4-methylnaphthalene-1-carboxylateYield 100.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Procedure

To a stirred solution of 4-methyl-naphthalene-1-carboxylic acid (10 g, 53.70 mmol) in dry DMF (50 mL) was added potassium carbonate (11.14 g, 80.55 mmol) at room temperature. Resulting reaction mixture was stirred for 30 minutes at room temperature. Then reaction mixture was cooled to 0° C. and methyl iodide (11.44 g, 3.04 mL, 80.55 mmol) was added dropwise. Resulting reaction mixture was stirred for 3 hours at room temperature. Progress of reaction was monitored by TLC using 10% EtOAc in hexane. Rf of new spot and stating material was 0.7 and 0.1, respectively. After consumption of starting material, reaction mixture was quenched with ice cold water (150 mL) and extracted with EtOAc (2×150 mL). Combined organic layer was washed with water (300 mL), brine (200 mL) and dried over sodium sulphate. Organic layer was evaporated in vacuo to afford orange colored thick oil. Crude compound was purified by column chromatography using 100-200 mesh silica gel. Desired compound was eluted in 9% in EtOAc in hexane to afford colorless liquid (10.85 g, 99%). 1H NMR (400 MHz, CDCl3) δ: 2.73 (s, 3H), 3.98 (S, 3H), 7.34 (d, J=7.4 Hz, 1H), 7.54-7.63 (m, 2H), 8.04 (d, J=7.92 Hz, 1H), 8.08 (d, J=7.44 Hz, 1H), 8.95 (d, J=8.12 Hz, 1H); LC-MS (m/z): =201.10 (M+H).

Workup

  1. customResulting
  2. customreaction mixture
  3. customThen reaction mixture
  4. temperaturewas cooled to 0° C.
  5. customResulting
  6. customreaction mixture
  7. stirringwas stirred for 3 hours at room temperature
  8. customProgress of reaction
  9. customAfter consumption of starting material, reaction mixture
  10. customwas quenched with ice cold water (150 mL)
  11. extractionextracted with EtOAc (2×150 mL)
  12. washCombined organic layer was washed with water (300 mL), brine (200 mL)
  13. dry with materialdried over sodium sulphate
  14. customOrganic layer was evaporated in vacuo
  15. customto afford orange colored thick oil
  16. customCrude compound was purified by column chromatography
  17. washDesired compound was eluted in 9% in EtOAc in hexane

Sources & evidence

ORD record
ord-a131d778a2d946d782e24a4608b35636
Source dataset
uspto-grants-2013_03
Patent number
US08404649B2

Reaction notes

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