Monomethyl terephthalate → HCID 15410718, compound

HRID 2233063Notes

Reaction equation

HRID 2233063 reaction equation
[CH3:1][N:2]([C:10]1[CH:19]=[CH:18][C:17]2[C:16]([CH3:21])([CH3:20])[CH2:15][CH2:14][C:13]([CH3:23])([CH3:22])[C:12]=2[CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH2:9].[CH3:24][O:25][C:26](=[O:36])[C:27]1[CH:35]=[CH:34][C:30]([C:31](O)=O)=[CH:29][CH:28]=1.O=P(Cl)(Cl)Cl>C1(C)C=CC=CC=1.CCOC(C)=O>[CH3:24][O:25][C:26](=[O:36])[C:27]1[CH:35]=[CH:34][C:30]([C:31]2[C:19]3=[CH:18][C:17]4[C:16]([CH3:21])([CH3:20])[CH2:15][CH2:14][C:13]([CH3:23])([CH3:22])[C:12]=4[CH:11]=[C:10]3[N:2]([CH3:1])[C:3]3[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=3[N:9]=2)=[CH:29][CH:28]=1

Participants

6

Reactant 3

HCID 15513Monomethyl terephthalateHCID 24813Phosphorus oxychlorideHCID 12042839HCID 12042839, compound

Product 1

HCID 15410718HCID 15410718, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of N-methyl-N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-1,2-phenylenediamine (13) (0.48 mol), terephthalic acid monomethyl ester (0.48 mol), and POCl3 (0.95 mol) in dry toluene (1750 mL) is heated at 80° C. for 4 days. After cooling to room temperature, the mixture is diluted with EtOAc (1500 mL). The mixture is washed with 5 N NaOH, brine, dried over MgSO4 and evaporated in vacuo. The residue is suspended in hexane. The crystals are collected by filtration and washed with hexane to give the ester (15) (R4=CH3, Z=H) as yellow solid.

Workup

  1. washThe mixture is washed with 5 N NaOH, brine
  2. dry with materialdried over MgSO4
  3. customevaporated in vacuo
  4. filtrationThe crystals are collected by filtration
  5. washwashed with hexane

Sources & evidence

ORD record
ord-8fe0320964964a3fab6f83666acac7f0
Source dataset
uspto-grants-2010_05
Patent number
US07709470B2

Reaction notes

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