Potassium Carbonate → 2-[3-(Decyloxy)-4-(3-hydroxypropyl)phenoxy]benzoic acid ethyl ester

HRID 982447Notes

Reaction equation

HRID 982447 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][CH2:20][OH:21])=[C:14]([OH:22])[CH:13]=1)[CH3:2].[CH2:24](I)[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33].C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[CH2:1]([O:3][C:4](=[O:23])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][CH2:20][OH:21])=[C:14]([O:22][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH:13]=1)[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 163141-IododecaneHCID 157180602-[3-Hydroxy-4-(3-hydroxypropyl)phenoxy]benzoic acid ethyl ester

Product 1

HCID 157180612-[3-(Decyloxy)-4-(3-hydroxypropyl)phenoxy]benzoic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 600 mg of 2-[3-hydroxy-4-(3-hydroxypropyl)phenoxy]benzoic acid ethyl ester, 0.4 ml of decyl iodide, and 0.26 g of potassium carbonate in 50 ml of methyl ethyl ketone was stirred at reflux overnight. After cooling to room temperature, the mixture was filtered and the filtrate concentrated in vacuo. Purification of the residue by column chromatography over silica gel eluting with 20% ethyl acetate in hexane provided 510 mg of the desired subtitled intermediate as an oil, MS, IR, NMR.

Workup

  1. temperatureat reflux overnight
  2. filtrationthe mixture was filtered
  3. concentrationthe filtrate concentrated in vacuo
  4. customPurification of the residue by column chromatography over silica gel eluting with 20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-528708b146c546d997190c9d3e1c2010
Source dataset
uspto-grants-1991_02
Patent number
US04996230

Reaction notes

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