Sodium Iodide → HCID 53797528, compound

HRID 488276Notes

Reaction equation

HRID 488276 reaction equation
[C:1]1([CH2:7][O:8][C:9](=[O:36])[C:10]2[CH:15]=[C:14]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][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][CH3:34])[CH:13]=[C:12]([OH:35])[CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:37]([O:39][CH2:40][CH2:41][O:42][CH2:43][CH2:44][O:45][CH2:46][CH2:47]Br)[CH3:38].[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.CN(C=O)C>[C:1]1([CH2:7][O:8][C:9](=[O:36])[C:10]2[CH:15]=[C:14]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][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][CH3:34])[CH:13]=[C:12]([O:35][CH2:47][CH2:46][O:45][CH2:44][CH2:43][O:42][CH2:41][CH2:40][O:39][CH2:37][CH3:38])[CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 14704176102684-61-7HCID 152334763-Hydroxy-5-(octadecyloxy)benzoic acid phenylmethyl ester

Product 1

HCID 53797528HCID 53797528, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2 g (4 mmol) of 3-hydroxy-5-(octadecyloxy)benzoic acid phenylmethyl ester, 3.65 g (15.8 mmol) of 2-[2-(2-ethoxyethoxy)ethoxy]ethyl bromide, 1.2 g (8 mmol) of sodium iodide and 2.2 g (16 mmol) of potassium carbonate in 60 ml of acetone and 30 ml of DMF was stirred at reflux for 40 hours. The usual workup followed by chromatography of the crude product on 200 g of silica gel using 40% ethyl acetate-hexane gave 1.76 g of 3-[2-[2-(2-ethoxyethoxy)ethoxy]ethoxy]-5-(octadecyloxy)benzoic acid phenylmethyl ester as an oil. The nmr and mass spectra were compatible with the structure.

Workup

  1. temperatureat reflux for 40 hours

Sources & evidence

ORD record
ord-cb56a5f6c8d84f578e9e332ee1b8b605
Source dataset
uspto-grants-1994_03
Patent number
US05298652

Reaction notes

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