1-Methyl-3-p-tolyltriazine → 3-Methyl-6-tetradecyloxy-benzofuran-2-carboxylic acid, methyl ester

HRID 903912Notes

Reaction equation

HRID 903912 reaction equation
[CH3:1][C:2]1[C:6]2[CH:7]=[CH:8][C:9]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:10][C:5]=2[O:4][C:3]=1[C:26]([OH:28])=[O:27].[CH3:29]N1C=CCN(C2C=CC(C)=CC=2)N1>CCOCC>[CH3:1][C:2]1[C:6]2[CH:7]=[CH:8][C:9]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:10][C:5]=2[O:4][C:3]=1[C:26]([O:28][CH3:29])=[O:27]

Participants

4

Reactant 2

HCID 202618531-Methyl-3-p-tolyltriazineHCID 233355643-Methyl-6-tetradecyloxybenzofuran-2-carboxylic acid

Product 1

HCID 867372773-Methyl-6-tetradecyloxy-benzofuran-2-carboxylic acid, methyl ester

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

0.4 g (1.03 mmoles) of 3-methyl-6-tetradecyloxy-benzofuran-2-carboxylic acid and 0.3 g (2.00 mmoles) of 1-methyl-3-p-tolyltriazine are stirred in ether and refluxed for 15 minutes. The mixture is then allowed to stand at room temperature for 1 hour. It is then refluxed for 15 minutes. The reaction mixture is worked-up by extraction with diethyl ether and HCl. The ether is distilled off and is replaced by dioxane. The resultant mixture is heated on a steam bath for 1 hour. It is then extracted with diethyl ether/HCl, H2O and NaHCO3 (aq.). The extract is evaporated and the ether replaced with methanol. The methyl ester of 3-methyl-6-tetradecyloxy-benzofuran-2-carboxylic acid is allowed to crystallize from the mixture.

Workup

  1. temperaturerefluxed for 15 minutes
  2. temperatureIt is then refluxed for 15 minutes
  3. extractionThe reaction mixture is worked-up by extraction with diethyl ether and HCl
  4. distillationThe ether is distilled off
  5. temperatureThe resultant mixture is heated on a steam bath for 1 hour
  6. extractionIt is then extracted with diethyl ether/HCl, H2O and NaHCO3 (aq.)
  7. customThe extract is evaporated
  8. customto crystallize from the mixture

Sources & evidence

ORD record
ord-5dc7e5a6466641e5a1a015b7266fe95d
Source dataset
uspto-grants-1980_10
Patent number
US04229467

Reaction notes

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