Iodoethane → HCID 14986448, compound

HRID 1613092Notes

Reaction equation

HRID 1613092 reaction equation
[OH:1][C:2]1[C:3]([CH3:30])=[C:4]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][O:16][C:17]2[CH:25]=[CH:24][C:20]([C:21]([OH:23])=[O:22])=[C:19]([OH:26])[C:18]=2[CH2:27][CH2:28][CH3:29])[CH:5]=[C:6]([CH3:9])[C:7]=1[OH:8].C(=O)(O)[O-].[Na+].[CH2:36](I)[CH3:37]>CN(C)C=O>[CH2:36]([O:22][C:21](=[O:23])[C:20]1[CH:24]=[CH:25][C:17]([O:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][C:4]2[CH:5]=[C:6]([CH3:9])[C:7]([OH:8])=[C:2]([OH:1])[C:3]=2[CH3:30])=[C:18]([CH2:27][CH2:28][CH3:29])[C:19]=1[OH:26])[CH3:37]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 516892Sodium BicarbonateHCID 14986421HCID 14986421, compound

Product 1

HCID 14986448HCID 14986448, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.170 g (1.68 mmole) of 4-[6-(3,4-dihydroxy-2,5-dimethylphenyl)hexyloxy]-2-hydroxy-3-propylbenzoic acid, 0.157 g (1.87 mmole) of sodium bicarbonate and 1.4 mL (16.8 mmole) of ethyl iodide in 10 mL of dimethylformamide was stirred at 50° for 10 hours. Workup as in Example 160 gave an oil which was purified by chromatography on 20 g of silica gel. Elution with 25% ethyl acetate-hexane gave the product which was recrystallized from hexane to give 0.50 g, mp 61°-64°, (67% yield) of 4-[6-(3,4-dihydroxy-2,5-dimethylphenyl)hexyloxy]-2-hydroxy-3-propylbenzoic acid ethyl ester.

Workup

  1. customWorkup as in Example 160 gave an oil which
  2. customwas purified by chromatography on 20 g of silica gel
  3. washElution with 25% ethyl acetate-hexane
  4. customgave the product which
  5. customwas recrystallized from hexane

Sources & evidence

ORD record
ord-8491153f2d264b8684f6e52bf7b5a15c
Source dataset
uspto-grants-1993_03
Patent number
US05191108

Reaction notes

Loading…