Acetone → 3-(Octadecyloxy)-5-[(5-methoxy-5-oxopentyl)oxy]benzoic acid phenylmethyl ester

HRID 1757811Notes

Reaction equation

HRID 1757811 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.Br[CH2:38][CH2:39][CH2:40][CH2:41][C:42]([O:44][CH3:45])=[O:43].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].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][CH2:38][CH2:39][CH2:40][CH2:41][C:42]([O:44][CH3:45])=[O:43])[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 5

HCID 180AcetoneHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 79557Methyl 5-bromovalerateHCID 152334763-Hydroxy-5-(octadecyloxy)benzoic acid phenylmethyl ester

Product 1

HCID 543871533-(Octadecyloxy)-5-[(5-methoxy-5-oxopentyl)oxy]benzoic acid phenylmethyl esterYield 92.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 10.0 g (0.02 mol) of 3-hydroxy-5-(octadecyloxy)benzoic acid phenylmethyl ester, 4.3 ml (0.03 mol) of methyl 5-bromovalerate, 5.6 g (0.04 mol) of potassium carbonate and 3.0 g (0.02 mol) of sodium iodide in300 ml of acetone and 75 ml of DMF was stirred at reflux under argon for 40hours. The reaction mixture was filtered and the filtrate was concentrated at reduced pressure to a solid which was recrystallized from methylene chloride-methanol to give 11.3 g (92% yield, mp 40°-42°) of 3-(octadecyloxy)-5-[(5-methoxy-5-oxopentyl)oxy]benzoic acid phenylmethyl ester. The structure was confirmed by nmr and mass spectra.

Workup

  1. temperatureat reflux under argon for 40hours
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated at reduced pressure to a solid which
  4. customwas recrystallized from methylene chloride-methanol

Sources & evidence

ORD record
ord-296246694d0b449287f2af0b245f844f
Source dataset
uspto-grants-1995_08
Patent number
US05446189

Reaction notes

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