Methyl iodide → HCID 18989160, compound

HRID 2395566Notes

Reaction equation

HRID 2395566 reaction equation
[CH2:1]([Li])CCC.[O:6]1[C:10]2[CH:11]=[CH:12][C:13]([C:15]([OH:17])=[O:16])=[CH:14][C:9]=2[O:8][CH2:7]1.CI.[OH-].[Na+]>O1CCCC1.O>[CH3:1][C:14]1[C:9]2[O:8][CH2:7][O:6][C:10]=2[CH:11]=[CH:12][C:13]=1[C:15]([OH:17])=[O:16]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 71961,3-Benzodioxole-5-carboxylic acidHCID 14798Sodium HydroxideHCID 178418339Butyllithium

Product 1

HCID 18989160HCID 18989160, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of n-butyllithium (5.1 ml of a 2.5M solution in hexanes) was added to a stirred suspension of 1,3-benzodioxole-5-carboxylic acid (1.0 g) in anhydrous tetrahydrofuran under an inert atmosphere keeping the temperature-below -60° C. The mixture was then stirred at -78° C. for 7 hours and methyl iodide (0.50 g) added and the mixture stirred at room temperature for 18 hours. The mixture was then treated with water and 2N sodium hydroxide. The aqueous phase was washed with ether, acidified and filtered. The solid was washed with hexane and dried to give 4-methyl-1,3-benzodioxole-5-carboxylic acid as a cream solid (0.91 g), m.p. 217°-219° C.

Workup

  1. customthe temperature-below -60° C
  2. stirringthe mixture stirred at room temperature for 18 hours
  3. washThe aqueous phase was washed with ether
  4. filtrationfiltered
  5. washThe solid was washed with hexane
  6. customdried

Sources & evidence

ORD record
ord-f35328311fe2489ea9f98da0b680a2f7
Source dataset
uspto-grants-1996_02
Patent number
US05489570

Reaction notes

Loading…