Methyl iodide → HCID 58298857, compound

HRID 453411Notes

Reaction equation

HRID 453411 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[C:5]([CH3:12])[C:4]=1[CH3:13].[Li][CH:15](CC)C.CI>O1CCCC1>[CH2:12]([C:5]1[C:4]([CH3:13])=[C:3]([O:2][CH3:1])[CH:11]=[CH:10][C:6]=1[C:7]([OH:9])=[O:8])[CH3:15]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 134400814-Methoxy-2,3-dimethylbenzoic acidHCID 178418400CID 53628100

Product 1

HCID 58298857HCID 58298857, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
78 °C

Procedure

2.50 g of 4-methoxy-2,3-dimethylbenzoic acid (G1) are dissolved in 160 ml of tetrahydrofuran under a nitrogen atmosphere and cooled to (−) 78° C. 11.5 ml of sec-BuLi are subsequently added dropwise at such a rate that the temperature of the reaction solution does not exceed (−) 65° C. When the addition is complete, the reddish reaction solution is stirred for a further 30 min with cooling. 3.59 ml of methyl iodide are then slowly added drop-wise. The cooling is subsequently removed, and the mixture is stirred for 1 h. For work-up, 160 ml of water are carefully added. The solution is subsequently extracted twice with 130 ml of ethyl acetate each time. The aqueous phase is cooled in an ice bath with stirring, acidified using 1.0 M HCl and filtered after 30 min. The filter cake is rinsed with cold water and subsequently recrystallised from 2-propanol. The crystals are filtered off with suction and dried for 2 h at 70° C. in vacuo, giving 1.90 g of the title compound as a colourless, crystalline solid having a melting point of 176.7° C.; MS: 194.2 (M+); TLC: Rf=0.29 (diethyl ether/petroleum ether 1:1 parts by volume).

Workup

  1. custom65° C
  2. additionWhen the addition
  3. temperaturewith cooling
  4. customThe cooling is subsequently removed
  5. stirringthe mixture is stirred for 1 h
  6. additionFor work-up, 160 ml of water are carefully added
  7. extractionThe solution is subsequently extracted twice with 130 ml of ethyl acetate each time
  8. temperatureThe aqueous phase is cooled in an ice bath
  9. stirringwith stirring
  10. filtrationfiltered after 30 min
  11. washThe filter cake is rinsed with cold water
  12. customsubsequently recrystallised from 2-propanol
  13. filtrationThe crystals are filtered off with suction
  14. customdried for 2 h at 70° C. in vacuo

Sources & evidence

ORD record
ord-d20e21e1a05a4c26b1fbcaff5adfbd33
Source dataset
uspto-grants-2013_07
Patent number
US08492440B2

Reaction notes

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