Trifluoroacetic acid → 3,5-Bis-phenyl-4-hydroxybenzoic acid methyl ester

HRID 1067316Notes

Reaction equation

HRID 1067316 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:8]([O:17]COCCOC)=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:10]=1)=[O:4].FC(F)(F)C(O)=O>C(Cl)Cl.CCOCC>[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]([OH:17])=[C:7]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:6]=1)=[O:4]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 541817672'-(2-Methoxyethoxymethoxy)-[1,1';3',1"]terphenyl-5'-carboxylic acid methyl ester

Product 1

HCID 543630073,5-Bis-phenyl-4-hydroxybenzoic acid methyl esterYield 99.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

At ambient temperature, to a stirred solution of 2′-(2-methoxyethoxymethoxy)-[1,1′;3′,1″]terphenyl-5′-carboxylic acid methyl ester (1.608 g, 4.098 mmol) in CH2Cl2 (16.08 mL) was added portionwise trifluoroacetic acid (16.08 mL). After 1 h, the reaction was diluted with ether (100 mL), washed sequentially with H2O (3×), with sat. aq. NaHCO3 (3×), with brine (3×), dried (MgSO4) and concentrated to give 1.240 g (99%) of the title compound as a white solid. 1H NMR (DMSO-d6) δ3.83 (s, 3H), 7.39-7.50 (m, 6H), 7.55-7.57 (m, 4H), 7.78 (s, 2H), 9.28 (s, 1H).

Workup

  1. washwashed sequentially with H2O (3×), with sat. aq. NaHCO3 (3×), with brine (3×)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-f8c9831fc5f84c66a97e3341348da173
Source dataset
uspto-grants-2001_06
Patent number
US06248764B1

Reaction notes

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