Sodium Hydroxide → 2'-(2-Methoxyethoxymethoxy)-[1,1';3',1"]terphenyl-5'-carboxylic acid

HRID 1871289Notes

Reaction equation

HRID 1871289 reaction equation
[OH-:1].[Na+].[CH3:3][O:4][CH2:5][CH2:6][O:7][CH2:8][O:9][C:10]1[C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:14][C:13]([CH:22]=[O:23])=[CH:12][C:11]=1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>O.C1COCC1.[Ag-]=O>[CH3:3][O:4][CH2:5][CH2:6][O:7][CH2:8][O:9][C:10]1[C:11]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[CH:12][C:13]([C:22]([OH:1])=[O:23])=[CH:14][C:15]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 222375093,5-Diphenyl-4-[(2-methoxyethoxy)methoxy]-benzaldehyde

Product 1

HCID 234456652'-(2-Methoxyethoxymethoxy)-[1,1';3',1"]terphenyl-5'-carboxylic acidYield 93%

Reagents, catalysts & solvents 3

HCID 178418778HCID 178418778, compoundCatalyst2×HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

At ambient temperature, to a stirred mixture of silver (I) oxide (0.570 g, 2.46 mmol) in H2O (9.8 mL) was added NaOH (0.983 g, 24.6 mmol) and the reaction was heated at 50° C. After 0.5 h, to the reaction was added a solution of 2'-(2-methoxyethoxymethoxy)-[1,1';3',1"]terphenyl-5'-carbaldehyde (1.78 g, 4.92 mmol) in THF (9.8 mL) and the reaction was heated at 90° C. for 1 h. To the reaction was added silver (I) oxide (0.570 g, 2.46 mmol), NaOH (0.983 g, 24.6 mmol) and H2O (10.0 mL). The reaction was heated at 90° C. for 16 h. The reaction was filtered through a celite pad, rinsing with hot H2O (3×). The filtrate was washed with ether (3×), acidified with 2N HCl (pH 2) and extracted with EtOAc. The organic extracts were dried (MgSO4) and concentrated to give 1.73 g (93%) of the title compound. 1H NMR (DMSO-d6) δ 2.77-2.80 (m, 2 H), 2.88-2.91 (m, 2 H), 3.01 (s, 3 H), 4.39 (s, 2 H), 7.39-7.52 (m, 6 H), 7.59-7.62 (m, 4 H), 7.89 (s, 2 H), 13.07 (s, 1 H).

Workup

  1. temperaturethe reaction was heated at 90° C. for 1 h
  2. temperatureThe reaction was heated at 90° C. for 16 h
  3. filtrationThe reaction was filtered through a celite pad
  4. washrinsing with hot H2O (3×)
  5. washThe filtrate was washed with ether (3×)
  6. extractionextracted with EtOAc
  7. dry with materialThe organic extracts were dried (MgSO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-69f670b02c814687993dc86d1c1afe07
Source dataset
uspto-grants-2000_08
Patent number
US06103708

Reaction notes

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