Methyl iodide → 2'-Methoxy-[1,1';3',1"]terphenyl-5'-carboxylic acid methyl ester

HRID 1280881Notes

Reaction equation

HRID 1280881 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:8]([OH:17])=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:10]=1)=[O:4].[C:24]([O-])([O-])=O.[K+].[K+].IC>O>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8]([O:17][CH3:24])=[C:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 543630073,5-Bis-phenyl-4-hydroxybenzoic acid methyl ester

Product 1

HCID 536767312'-Methoxy-[1,1';3',1"]terphenyl-5'-carboxylic acid methyl esterYield 99%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

At ambient temperature, to a stirred mixture containing 2′-hydroxy-[1,1′;3′,1″]terphenyl-5′-carboxylic acid methyl ester (1.232 g, 4.049 mmol) and K2CO3 (0.6155 g, 4.454 mmol) in N,N-DMF (10.1 mL) was added iodomethane (0.353 mL, 5.67 mmol). After 18 h, the reaction was diluted with H2O (100 mL) and the reaction was stirred vigorously. The resulting precipitate was collected, dissolved in CH2Cl2, dried (K2CO3) and concentrated to give 1.167 g, (99%) of the title compound. 1H NMR (DMSO-d6) δ 3.16 (s, 3H), 3.87 (s, 3H), 7.41-7.53 (m, 6H), 7.58-7.60 (m, 4H), 7.89 (s, 2H).

Workup

  1. customThe resulting precipitate was collected
  2. dissolutiondissolved in CH2Cl2
  3. dry with materialdried (K2CO3)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ebfd6671b8934ab09335af801ed7cb35
Source dataset
uspto-grants-2002_09
Patent number
US06451845B1

Reaction notes

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