Methyl iodide → HCID 13853500, compound

HRID 542497Notes

Reaction equation

HRID 542497 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:14]=[C:13]([OH:15])[CH:12]=[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:5]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17].CI.[CH3:23]N(P(N(C)C)(N(C)C)=O)C>O1CCCC1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:3][C:4]1[CH:14]=[C:13]([O:15][CH3:23])[CH:12]=[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:5]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 12679HexamethylphosphoramideHCID 24758Sodium hydrideHCID 13853499HCID 13853499, compound

Product 1

HCID 13853500HCID 13853500, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Sodium hydride (380 mg. 50% oil) was added portionwise to a solution of diethyl 3-methyl-5-hydroxyphthalate (2 gm) in dry tetrahydrofuran (50 ml). The solution was stirred for 30 minutes. Methyl iodide (2 ml), tetra-n-butylammonium iodide (45 mg) and HMPA (5 ml) was added. The solution was stirred at room temperature for 21/2 hours at refluxed at 60° C. for 1 hour. The solvent was removed under reduced pressure. The oil was partitioned between ethyl acetate and 5% hydrochloric acid solution. The ethyl acetate layer was washed with brine solution and dried over magnesium sulphate. Solvent evaporation gave an oil which was chromatographed (20% ethyl acetate:petroleum ether) to give diethyl 3-methyl-5-methoxy-phthalate.

Workup

  1. stirringThe solution was stirred at room temperature for 21/2 hours
  2. customThe solvent was removed under reduced pressure
  3. customThe oil was partitioned between ethyl acetate and 5% hydrochloric acid solution
  4. washThe ethyl acetate layer was washed with brine solution
  5. dry with materialdried over magnesium sulphate
  6. customSolvent evaporation
  7. customgave an oil which
  8. customwas chromatographed (20% ethyl acetate:petroleum ether)

Sources & evidence

ORD record
ord-5b8b4b98dd5f4232bc154381731964cd
Source dataset
uspto-grants-1987_04
Patent number
US04657893

Reaction notes

Loading…