Sodium Hydroxide → HCID 54312565, compound

HRID 53286Notes

Reaction equation

HRID 53286 reaction equation
[CH3:1][C:2]1([CH3:29])[C:10]2[C:5](=[CH:6][C:7]([CH:11]=[CH:12][C:13]3[CH:22]=[CH:21][C:16]([C:17]([O:19]C)=[O:18])=[CH:15][CH:14]=3)=[CH:8][CH:9]=2)[C:4]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:3]1.[OH-].[Na+]>O1CCCC1.CO>[CH3:1][C:2]1([CH3:29])[C:10]2[C:5](=[CH:6][C:7]([CH:11]=[CH:12][C:13]3[CH:22]=[CH:21][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=3)=[CH:8][CH:9]=2)[C:4]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:3]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 54011914Methyl 4-[2-(1,1-dimethyl-3-phenyl-1H-inden-5-yl)-vinyl]benzoate

Product 1

HCID 54312565HCID 54312565, compoundYield 97.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 4-[2-(1,1-dimethyl-3-phenyl-1H-inden-5-yl)-vinyl]benzoate (294 mg, 0.77 mmol) and 0.77 mL of 10N NaOH in 7 mL of tetrahydrofuran and 5 mL of methanol were stirred at reflux for 1 hour. The mixture was concentrated and acidified with 1N HCl (10 mL), extracted with ethyl acetate (30 mL×2). The combined extracts were washed with water (10 mL), dried over magnesium sulfate, and evaporated. The residue was triturated in hot methanol to give 276 mg (90% yield) of the title compound which contained a molecule of methanol; 1H-NMR (DMSO-d6) δ1.34 (s, 6H), 3.14 (s, 3H), 6.58 (s, 1H), 7.25 (d, J=16.4 Hz, 1H), 7.37-7.71 (m, 11H), 7.90 (d, J=8.3 Hz, 2H); MS m/e 367 (MH+).

Workup

  1. temperatureat reflux for 1 hour
  2. concentrationThe mixture was concentrated
  3. extractionextracted with ethyl acetate (30 mL×2)
  4. washThe combined extracts were washed with water (10 mL)
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customThe residue was triturated in hot methanol

Sources & evidence

ORD record
ord-e9c09308defc463c92f639b072603505
Source dataset
uspto-grants-1997_04
Patent number
US05618839

Reaction notes

Loading…