Methanol → 4-[1 (5-Methyl-thien-2-yl)3,4-dihydro-4,4-dimethyl-anthracen-8-yl]-benzoic acid

HRID 1375266Notes

Reaction equation

HRID 1375266 reaction equation
[CH3:1][C:2]1[S:6][C:5]([C:7]2[C:20]3[C:11](=[CH:12][C:13]4[C:18]([CH:19]=3)=[C:17]([C:21]3[CH:31]=[CH:30][C:24]([C:25]([O:27]CC)=[O:26])=[CH:23][CH:22]=3)[CH:16]=[CH:15][CH:14]=4)[C:10]([CH3:33])([CH3:32])[CH2:9][CH:8]=2)=[CH:4][CH:3]=1.CO.[Li+].[OH-].O>C1COCC1>[CH3:1][C:2]1[S:6][C:5]([C:7]2[C:20]3[C:11](=[CH:12][C:13]4[C:18]([CH:19]=3)=[C:17]([C:21]3[CH:22]=[CH:23][C:24]([C:25]([OH:27])=[O:26])=[CH:30][CH:31]=3)[CH:16]=[CH:15][CH:14]=4)[C:10]([CH3:33])([CH3:32])[CH2:9][CH:8]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 3939Lithium HydroxideHCID 18620054Ethyl 4-[1-(5-methyl-thien-2-yl)-3,4-dihydro 4,4-dimethyl-anthracen-8-yl]-benzoate2×

Product 1

HCID 186200524-[1 (5-Methyl-thien-2-yl)3,4-dihydro-4,4-dimethyl-anthracen-8-yl]-benzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of ethyl 4-[1-(5-methyl-thien-2-yl)-3,4-dihydro-4,4-dimethyl-anthracen-8-yl]-benzoate (Compound 3, 33 mg, 0.07 mmol), in THF (2 mL), MeOH (2 mL), was added aqueous LiOH (1M solution, 0.2 mL, 0.2 mmol). After 16 hours, water (2 mL) was added to the reaction mixture, about 50% of the organic solvents were removed by distillation, and the mixture was further diluted the mixture with water (5 mL). The reaction mixture was washed with ether (10 mL) and the aqueous layer was acidified to pH 4 and extracted with ethyl acetate (3×20 m). The combined organic layers were washed water (5 mL), brine (10 mL), dried with MgSO4 and the solvent was removed by distillation. The product was recrystallized from acetone to obtain the title compound as a white solid.

Workup

  1. customwere removed by distillation
  2. additionthe mixture was further diluted the mixture with water (5 mL)
  3. washThe reaction mixture was washed with ether (10 mL)
  4. extractionextracted with ethyl acetate (3×20 m)
  5. washThe combined organic layers were washed water (5 mL), brine (10 mL)
  6. dry with materialdried with MgSO4
  7. customthe solvent was removed by distillation
  8. customThe product was recrystallized from acetone

Sources & evidence

ORD record
ord-a5ec3a3f67624c63906f38f772f80634
Source dataset
uspto-grants-2007_01
Patent number
US07166726B2

Reaction notes

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