Water → 4-(4-(3,5-Bis(4-(4-carboxyphenyl)phenyl)phenyl)phenyl)benzoic acid

HRID 78865Notes

Reaction equation

HRID 78865 reaction equation
[C:1]1([C:39]2[CH:44]=[CH:43][C:42]([C:45]3[CH:54]=[CH:53][C:48]([C:49]([O:51]C)=[O:50])=[CH:47][CH:46]=3)=[CH:41][CH:40]=2)[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[CH:22]=[CH:21][C:16]([C:17]([O:19]C)=[O:18])=[CH:15][CH:14]=3)=[CH:9][CH:8]=2)[CH:4]=[C:3]([C:23]2[CH:28]=[CH:27][C:26]([C:29]3[CH:38]=[CH:37][C:32]([C:33]([O:35]C)=[O:34])=[CH:31][CH:30]=3)=[CH:25][CH:24]=2)[CH:2]=1.[OH-].[Na+].C1COCC1.O>CO>[C:1]1([C:39]2[CH:44]=[CH:43][C:42]([C:45]3[CH:46]=[CH:47][C:48]([C:49]([OH:51])=[O:50])=[CH:53][CH:54]=3)=[CH:41][CH:40]=2)[CH:6]=[C:5]([C:7]2[CH:8]=[CH:9][C:10]([C:13]3[CH:14]=[CH:15][C:16]([C:17]([OH:19])=[O:18])=[CH:21][CH:22]=3)=[CH:11][CH:12]=2)[CH:4]=[C:3]([C:23]2[CH:24]=[CH:25][C:26]([C:29]3[CH:38]=[CH:37][C:32]([C:33]([OH:35])=[O:34])=[CH:31][CH:30]=3)=[CH:27][CH:28]=2)[CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 68008686Trimethyl 4,4',4''-(benzene-1,3,5-triyl-tris(benzene-4,1-diyl))tribenzoate

Product 1

HCID 595672024-(4-(3,5-Bis(4-(4-carboxyphenyl)phenyl)phenyl)phenyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Trimethyl 4,4′,4″-(benzene-1,3,5-triyl-tris(benzene-4,1-diyl))tribenzoate (2.00 g, 2.82 mmol), 2.2 g of NaOH, THF, water, and methanol (200, 80, and 50 mL, respectively) were mixed in a 1 L round bottom flask equipped with a magnetic stirring bar, and the mixture was stirred for 2 days at room temperature. The solution was evaporated under vacuum. The residue was acidified with 3 M HCl. The white solid was collected by filtration, washed with methylene chloride and methanol and dried in vacuum overnight (1.80 g, 96%): mp 326° C.; 1H-NMR (DMSO-d6, 400 MHz) δ 13.07 (br, 3H) 8.07 (d, 6H, J=8.0 Hz), 8.06 (s, 3H), 8.05 (d, 6H, J=8.0 Hz), 7.91 (d, 6H, J=7.6 Hz), 7.89 (d, 6H, J=7.2 Hz); 13C-NMR (DMSO-d6, 100 MHz) δ 168.0, 144.6, 141.9, 140.7, 139.2, 130.9, 130.6, 128.8, 128.4, 127.6, 125.3; FT-IR (KBr, 4000-400 cm−1) 3448 (br), 3029 (br), 2661 (w), 2536 (w), 1925 (w), 1686 (s), 1606 (s), 1419 (m), 1276 (m), 1177 (m), 1118 (m), 1003 (m), 824 (s), 773 (s); MALDI-TOF MS (m/z) [M]+ 666.2976 (found), 666.2042 (calcd. for C45H30O6).

Workup

  1. customequipped with a magnetic stirring bar
  2. customThe solution was evaporated under vacuum
  3. filtrationThe white solid was collected by filtration
  4. washwashed with methylene chloride and methanol
  5. customdried in vacuum overnight (1.80 g, 96%)

Sources & evidence

ORD record
ord-7ebbb5f61f59443caa39440ff0526b42
Source dataset
uspto-grants-2014_09
Patent number
US08841471B2

Reaction notes

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