Citric Acid → (E)-3-(dimethylamino)-5-(4-(methoxymethoxy)-3,5-dimethylstyryl)benzoic acid

HRID 2368876Notes

Reaction equation

HRID 2368876 reaction equation
[CH3:1][N:2]([CH3:28])[C:3]1[CH:4]=[C:5]([CH:11]=[C:12](/[CH:14]=[CH:15]/[C:16]2[CH:21]=[C:20]([CH3:22])[C:19]([O:23][CH2:24][O:25][CH3:26])=[C:18]([CH3:27])[CH:17]=2)[CH:13]=1)[C:6]([O:8]CC)=[O:7].[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1.CCO.CCOC(C)=O>[CH3:28][N:2]([CH3:1])[C:3]1[CH:4]=[C:5]([CH:11]=[C:12](/[CH:14]=[CH:15]/[C:16]2[CH:17]=[C:18]([CH3:27])[C:19]([O:23][CH2:24][O:25][CH3:26])=[C:20]([CH3:22])[CH:21]=2)[CH:13]=1)[C:6]([OH:8])=[O:7]

Participants

7

Reactant 3

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 68335176(E)-Ethyl 3-(dimethylamino)-5-(4-(methoxymethoxy)-3,5-dimethylstyryl)benzoate

Product 1

HCID 67262210(E)-3-(dimethylamino)-5-(4-(methoxymethoxy)-3,5-dimethylstyryl)benzoic acidYield 97%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of Compound 4 (1.046 g, 2.728 mmol) in THF and EtOH ( 8/4 mL) was added 2 N NaOH (2.728 mL, 5.456 mmol) at room temperature. The reaction mixture was stirred overnight (about 18 hours) at room temperature and diluted with EtOAc and acidified with 5% citric acid. The solution was washed with saturated brine and dried with Na2SO4. The solution was filtered and concentrated. Compound 5 (0.94 g, 97%) was obtained without further purification (TLC indicated a pure compound). 1H-NMR (500 MHz, DMSO-d6) δ 7.47 (s, 1H), 7.31 (s, 2H), 7.12-7.16 (m, 4H), 4.94 (s, 2H), 3.51 (s, 3H), 2.98 (s, 6H), 2.25 (s, 6H); 13C-NMR (125 MHz, DMSO-d6) δ 167.75, 154.18, 150.47, 137.92, 132.56, 131.62, 130.63, 128.12, 127.43, 126.86, 114.89, 114.16, 111.62, 98.51, 56.71, 40.03, 16.55; ESI-MS: m/z (MH+): 356.1856 (calc'd), 356.1854 (found).

Workup

  1. washThe solution was washed with saturated brine
  2. dry with materialdried with Na2SO4
  3. filtrationThe solution was filtered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-aa8fc085be49425fb6dba6653afdbbeb
Source dataset
uspto-grants-2014_04
Patent number
US08703815B2

Reaction notes

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