Dimethyl terephthalate → Methyl 4-(dodecylcarbamoyl)benzoate

HRID 236057Notes

Reaction equation

HRID 236057 reaction equation
[C:1]([O:13][CH3:14])(=[O:12])[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8]C)=O)=[CH:4][CH:3]=1.[CH2:15]([NH2:27])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].C(N(CCCCCCCCCCCC)C(=O)C1C=CC(C(O)=O)=CC=1)CCCCCCCCCCC>CO>[CH2:15]([NH:27][C:6](=[O:8])[C:5]1[CH:4]=[CH:3][C:2]([C:1]([O:13][CH3:14])=[O:12])=[CH:11][CH:10]=1)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

5

Reactant 3

HCID 8441Dimethyl terephthalateHCID 13583DodecylamineHCID 70436535Terephthalic acid bisdodecylamide

Product 1

HCID 53996922Methyl 4-(dodecylcarbamoyl)benzoateYield 91.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

19.4 g (0.1 mole) of dimethyl terephthalate and 18.5 g (0.1 mole) of dodecylamine are refluxed in 100 ml of methanol. After addition of 9 g (0.05 mole) of sodim methylate (30% strength in methanol) refluxing is continued for 8 hours, and the reaction batch is then worked up as described in Example 1, affording 31.7 g (91.2%) of 4-carbomethoxybenzoic acid dodecylamide having a 14% terephthalic acid bisdodecylamide content.

Workup

  1. temperaturerefluxing

Sources & evidence

ORD record
ord-3d753371c69649b296fea20ea0f9e40d
Source dataset
uspto-grants-1987_02
Patent number
US04642375

Reaction notes

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