Sodium Hydroxide → 1-hydroxy-6-methoxy-1-methyl-3-phenyl-1H-indene-2-carboxylic acid

HRID 19542Notes

Reaction equation

HRID 19542 reaction equation
C([O:3][C:4]([C:6]1[C:7]([OH:24])([CH3:23])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][CH:11]=[C:10]([O:21][CH3:22])[CH:9]=2)=[O:5])C.[OH-].[Na+]>C1COCC1.C(O)C>[OH:24][C:7]1([CH3:23])[C:8]2[C:13](=[CH:12][CH:11]=[C:10]([O:21][CH3:22])[CH:9]=2)[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:6]1[C:4]([OH:5])=[O:3]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 116312001-hydroxy-6-methoxy-1-methyl-3-phenyl-1H-indene-2-carboxylic acid ethyl ester

Product 1

HCID 117163251-hydroxy-6-methoxy-1-methyl-3-phenyl-1H-indene-2-carboxylic acidYield 69%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

1-Hydroxy-6-methoxy-1-methyl-3-phenyl-1H-indene-2-carboxylic acid ethyl ester (100 mg, 0.309 mmol) prepared in Example 4 was dissolved in THF, and an excess amount of sodium hydroxide dissolved in aqueous ethanol was added thereto in such a way not to cause layer separation. The mixture was stirred for 24 hrs at RT, and the pH was adjusted to 3˜4 using 2N hydrochloric acid. The resulting mixture was extracted with ethyl acetate. The organic layer was separated, dried over anhydrous MgSO4 and concentrated under a reduced pressure, to obtain 63 mg of the titled compound (yield: 69%).

Workup

  1. additionwas added
  2. customlayer separation
  3. extractionThe resulting mixture was extracted with ethyl acetate
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated under a reduced pressure

Sources & evidence

ORD record
ord-903b09499dbd41e4a185bb24d32712d2
Source dataset
uspto-grants-2010_06
Patent number
US07745439B2

Reaction notes

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