Methyl iodide → HCID 15233468, compound

HRID 1492868Notes

Reaction equation

HRID 1492868 reaction equation
[OH:1][C:2]1[CH:40]=[CH:39][C:5]([O:6][CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:12]=[C:13]([CH:17]=[C:18]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[CH:19]=2)[C:14]([OH:16])=[O:15])=[CH:4][CH:3]=1.[C:41](=O)(O)[O-].[Na+].CI>CN(C=O)C>[CH3:41][O:15][C:14](=[O:16])[C:13]1[CH:17]=[C:18]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[CH:19]=[C:11]([O:10][CH2:9][CH2:8][CH2:7][O:6][C:5]2[CH:4]=[CH:3][C:2]([OH:1])=[CH:40][CH:39]=2)[CH:12]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 516892Sodium BicarbonateHCID 18951581HCID 18951581, compound

Product 1

HCID 15233468HCID 15233468, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.30 g (0.54 mmol) of 3-[3-(4-hydroxyphenoxy) propoxy]-5-(octadecyloxy)benzoic acid, 0.14 g (1.62 mmol) of sodium bicarbonate and 0.67 ml (10.8 mmol) of methyl iodide in 5 ml of DMF was stirred and heated at 40° for 48 hours. The solvent was removed at reduced pressure, the residue was extracted with ethyl acetate and the extract was washed with water. The dried extract was concentrated to a solid which was triturated with hexane and filtered to give 0.298 g (97% yield, mp 88°-90°) of 3-[3-(4-hydroxyphenoxy)propoxy]-5-(octadecyloxy)benzoic acid methyl ester.

Workup

  1. temperatureheated at 40° for 48 hours
  2. customThe solvent was removed at reduced pressure
  3. extractionthe residue was extracted with ethyl acetate
  4. washthe extract was washed with water
  5. extractionThe dried extract
  6. concentrationwas concentrated to a solid which
  7. customwas triturated with hexane
  8. filtrationfiltered

Sources & evidence

ORD record
ord-b977c462dc3a464081b1cf85bfe9ac43
Source dataset
uspto-grants-1994_12
Patent number
US05374772

Reaction notes

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