Ethanol → HCID 23686548, compound

HRID 1456866Notes

Reaction equation

HRID 1456866 reaction equation
C(O)C.[CH3:4][C:5]([CH3:46])([CH:9]([C:28]1[CH:33]=[CH:32][C:31]([O:34][CH2:35][C:36]2[CH:45]=[CH:44][C:43]3[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=3)[N:37]=2)=[CH:30][CH:29]=1)[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]2[CH:27]=[CH:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19]=2)=[CH:12][CH:11]=1)[C:6]([OH:8])=[O:7].[OH-].[Na+:48]>C1COCC1>[Na+:48].[CH3:4][C:5]([CH3:46])([CH:9]([C:28]1[CH:33]=[CH:32][C:31]([O:34][CH2:35][C:36]2[CH:45]=[CH:44][C:43]3[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=3)[N:37]=2)=[CH:30][CH:29]=1)[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]2[CH:27]=[CH:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19]=2)=[CH:12][CH:11]=1)[C:6]([O-:8])=[O:7]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 10698648HCID 10698648, compound

Product 1

HCID 23686548HCID 23686548, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution in THF (10 mL) and ethanol (8 mL) of 2,2-dimethyl-3,3-bis(4-(2-quinolylmethoxy)phenyl)propionic acid (0.128 g, 0.225 mmol), prepared as in step 3, was added one equivalent of NaOH (2.3 mL, 0.1N NaOH). The reaction was stirred for 1 hour at room temperature, concentrated, and dried under high vacuum to provide 2,2-dimethyl-3,3-bis(4-(2-quinolylmethoxy)phenyl)propionic acid sodium salt as a white powder 0.13 g (99%): mp 250°-255° C. (dec); 1H NMR (300 MHz, DMSO-d6) d 0.91 (s, 6H), 4.46 (s, 1H), 5.29 (s, 4H), 6.87 (d, 4H, J=9 Hz), 7.15 (d, 4H, J=9 Hz), 7.61 (m, 2H), 7.67 (d, 4H, J=9 Hz), 7.78 (m, 2H), 8.00 (t, 4H, J=9 Hz), 8.40 (d, 2H, J=9 Hz); MS m/e (FAB+) 569 (M+H)+, (FAB-) 567 (M-H)-. Anal. Calc'd. for C37H31N2O4Na.0.5 H2O: C, 74.10; H, 5.37; N 4.67. Found C, 74.02; H, 5.24; N, 4.50.

Workup

  1. concentrationconcentrated
  2. customdried under high vacuum

Sources & evidence

ORD record
ord-96062c73657b402e8959ef0244059717
Source dataset
uspto-grants-1998_12
Patent number
US05843968

Reaction notes

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