Sodium Iodide → 3-(Octadecyloxy)-5-(3-phenoxypropoxy)benzoic acid phenylmethyl ester

HRID 488257Notes

Reaction equation

HRID 488257 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.[O:37]([CH2:44][CH2:45][CH2:46]Br)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.[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:11]=[C:12]([O:35][CH2:46][CH2:45][CH2:44][O:37][C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[CH:13]=[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:15]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 68522Benzene, (3-bromopropoxy)-HCID 152334763-Hydroxy-5-(octadecyloxy)benzoic acid phenylmethyl ester

Product 1

HCID 152328333-(Octadecyloxy)-5-(3-phenoxypropoxy)benzoic acid phenylmethyl esterYield 96.4%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 12 g (0.024 mol) of 3-hydroxy-5-(octadecyloxy)benzoic acid phenylmethyl ester, 6 ml (0.038 mol) of 3-phenoxypropyl bromide, 3.6 g (0.024 mol) of sodium iodide and 10 g (0.072 mol) of potassium carbonate in 400 ml of acetone and 80 ml of DMF was stirred at reflux for 46 hours. The reaction mixture was filtered and the filtrate was concentrated to dryness at reduced pressure. Water was added to the residue and the product was extracted with ethyl acetate. The dried extract was concentrated at reduced pressure to an oil which was purified by HPLC using 5% ethyl acetate-hexane. The pure fractions were combined, triturated with hexane and filtered to give 14.6 g (96% yield, mp 46°-47°) of 3-(octadecyloxy)-5-(3-phenoxypropoxy)benzoic acid phenylmethyl ester. The structure was confirmed by nmr and mass spectra.

Workup

  1. temperatureat reflux for 46 hours
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated to dryness at reduced pressure
  4. additionWater was added to the residue
  5. extractionthe product was extracted with ethyl acetate
  6. extractionThe dried extract
  7. concentrationwas concentrated at reduced pressure to an oil which
  8. customwas purified by HPLC
  9. customtriturated with hexane
  10. filtrationfiltered

Sources & evidence

ORD record
ord-e3349e6c12f2490fa57e84acde8e6ec1
Source dataset
uspto-grants-1994_03
Patent number
US05298652

Reaction notes

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