Methyl iodide → 3-[[6-(2,3-Dihydroxyphenyl)hexyl]oxy]-5-(octadecyloxy)benzoic acid methyl ester

HRID 1492867Notes

Reaction equation

HRID 1492867 reaction equation
[OH:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][C:16]1[CH:17]=[C:18]([CH:22]=[C:23]([O: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][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[CH:24]=1)[C:19]([OH:21])=[O:20].[C:44](=O)(O)[O-].[Na+].CI>CN(C=O)C>[CH3:44][O:20][C:19](=[O:21])[C:18]1[CH:22]=[C:23]([O: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][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[CH:24]=[C:16]([O:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][C:3]2[CH:4]=[CH:5][CH:6]=[C:7]([OH:8])[C:2]=2[OH:1])[CH:17]=1

Participants

5

Reactant 3

HCID 6328Methyl iodide2×HCID 516892Sodium Bicarbonate2×HCID 98516283-[[6-(2,3-Dihydroxyphenyl) hexyl]oxy]-5-(octadecyloxy)benzoic acid

Product 1

HCID 542033863-[[6-(2,3-Dihydroxyphenyl)hexyl]oxy]-5-(octadecyloxy)benzoic acid methyl esterYield 68%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.15 g (0.25 mmol) of 3-[[6-(2,3-dihydroxyphenyl) hexyl]oxy]-5-(octadecyloxy)benzoic acid, 0.05 g (0.6 mmol) of sodium bicarbonate and 0.64 ml (10 mmol) of methyl iodide in 3 ml of DMF was stirred and heated at 40° for 5 days. An additional 0.32 ml of methyl iodide and 0.05 g of sodium bicarbonate were added and heating at 40° was continued for 6 days. 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 an oil which was purified by chromatography on 4 g of silica gel using 25% ethyl acetate-hexane to give 0.104 g (68% yield, mp 82°-84°) of 3-[[6-(2,3-dihydroxyphenyl)hexyl]oxy]-5-(octadecyloxy)benzoic acid methyl ester.

Workup

  1. temperatureheated at 40° for 5 days
  2. temperatureheating at 40°
  3. customThe solvent was removed at reduced pressure
  4. extractionthe residue was extracted with ethyl acetate
  5. washthe extract was washed with water
  6. extractionThe dried extract
  7. concentrationwas concentrated to an oil which
  8. customwas purified by chromatography on 4 g of silica gel using 25% ethyl acetate-hexane

Sources & evidence

ORD record
ord-300fba6623d8429b84a1c8fb19549d50
Source dataset
uspto-grants-1994_12
Patent number
US05374772

Reaction notes

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