Methanol → HCID 59188282, compound

HRID 2369461Notes

Reaction equation

HRID 2369461 reaction equation
[CH2:1]([CH:11]([CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH3:62])[C:12]([NH:14][C:15]1[CH:16]=[C:17]([CH:22]=[C:23]([NH:25][C:26](=[O:50])[CH:27]([CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[CH:24]=1)[C:18]([O:20]C)=[O:19])=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[OH-].[K+].CO.O>C(OCC)C>[CH2:1]([CH:11]([CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH3:62])[C:12]([NH:14][C:15]1[CH:16]=[C:17]([CH:22]=[C:23]([NH:25][C:26](=[O:50])[CH:27]([CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[CH:24]=1)[C:18]([OH:20])=[O:19])=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 14797Potassium HydroxideHCID 67065126HCID 67065126, compound

Product 1

HCID 59188282HCID 59188282, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Methyl 3,5-bis(2′-decyltetradecanamido)benzoate from Step II, potassium hydroxide (0.38 g, 5.77 mmol), and methanol (20 mL) are added to a 50 mL vessel and heated to reflux. Deionized water (10 mL) is then added and the reaction is held at reflux overnight. The reaction is then cooled to room temperature, which results in the formation of an oil phase. Diethyl ether (20 mL) is added, and the aqueous phase is removed. The organic phase is then washed successively with 1 M hydrochloric acid (30 mL), 0.1 M hydrochloric acid (30 mL), and deionized water twice (30 mL each), before concentrating the ether layer by rotary evaporation, and drying in vacuo to give 3,5-bis(2′-decyltetradecanamido)benzoic acid as a light brown waxy solid (1.33 g, 99%). The product is identified by 1H and 13C NMR spectroscopy and ESI-MS and is of satisfactory purity.

Workup

  1. temperatureheated to reflux
  2. temperatureat reflux overnight
  3. customwhich results in the formation of an oil phase
  4. customthe aqueous phase is removed
  5. washThe organic phase is then washed successively with 1 M hydrochloric acid (30 mL), 0.1 M hydrochloric acid (30 mL)
  6. concentrationbefore concentrating the ether layer
  7. customby rotary evaporation
  8. customdrying in vacuo

Sources & evidence

ORD record
ord-80943452e0644af9813bb43ffa857aed
Source dataset
uspto-grants-2014_04
Patent number
US08703988B2

Reaction notes

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