Sodium Hydroxide → 4-[1,1-Dimethyl-3-phenyl-1H-inden-5-yloxymethyl)benzoic acid

HRID 53284Notes

Reaction equation

HRID 53284 reaction equation
[CH3:1][C:2]([O:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[CH2:20][CH:19]=[C:18]2[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10]C)=[O:9])=[CH:6][CH:5]=1)[CH3:3].[OH-].[Na+]>O1CCCC1.CO>[CH3:3][C:2]([O:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[CH2:20][CH:19]=[C:18]2[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:4]1[CH:5]=[CH:6][C:7]([C:8]([OH:10])=[O:9])=[CH:12][CH:13]=1)[CH3:1]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22356918HCID 22356918, compound

Product 1

HCID 190344314-[1,1-Dimethyl-3-phenyl-1H-inden-5-yloxymethyl)benzoic acidYield 85.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 4-(1,1-dimethyl-3-phenyl-1H-inden-5-yloxymethyl)benzoate (300 mg, 0.78 mmol) and 3.9 mL of 2N NaOH in 5 mL of tetrahydrofuran and 5 mL of methanol were stirred at room temperature for 16 hours. The mixture was concentrated and acidified with 1N HCl (10 mL), extracted with ethyl acetate (20 mL×3). The combined extracts were washed with water (10 mL), dried over magnesium sulfate, and evaporated. The residue was crystallized from ether-hexane to give 247 mg (85% yield) of the title compound as white crystals; 1H-NMR (DMSO-d6) δ1.31 (s, 6H), 5.20 (s, 2H), 6.57 (s, 1H), 6.89 (dd, J=1.1, 8.2 Hz, 1H), 7.02 (d, J=1.1 Hz, 1H), 7.36-7.57 (m, 8H), 7.95 (d, J=8.3 Hz, 2H), 12.94 (bs, 1H) ; MS m/e 371 (MH+).

Workup

  1. concentrationThe mixture was concentrated
  2. extractionextracted with ethyl acetate (20 mL×3)
  3. washThe combined extracts were washed with water (10 mL)
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue was crystallized from ether-hexane

Sources & evidence

ORD record
ord-d63eacd184524d699a45430f8bde7fed
Source dataset
uspto-grants-1997_04
Patent number
US05618839

Reaction notes

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