Methanol → HCID 59188282, compound

HRID 2176728Notes

Reaction equation

HRID 2176728 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 2, potassium hydroxide (0.38 g, 5.77 mmol), and methanol (20 mL) were added to a 50 mL vessel and heated to reflux. Deionized water (10 mL) was then added and the reaction was held at reflux overnight. The reaction was then cooled to room temperature, which resulted in the formation of an oil phase. Diethyl ether (20 mL) was added and the aqueous phase was removed. The organic phase was then washed successively with 1 Molar hydrochloric acid (30 mL), 0.1 Molar 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 was identified by 1H and 13C NMR spectroscopy and ESI-MS and was of satisfactory purity. The product was believed to be of the formula

Workup

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

Sources & evidence

ORD record
ord-bd8507e2494346258b730e0e2d9f7be6
Source dataset
uspto-grants-2015_06
Patent number
US09067878B2

Reaction notes

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