Potassium Hydroxide → 2-Carboxy-2-(4-methoxybenzylthio)indan

HRID 1451237Notes

Reaction equation

HRID 1451237 reaction equation
[C:1]([C:5]1([S:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6]1)([O:3]C)=[O:2].[OH-].[K+]>C(O)C.O.O1CCCC1>[C:1]([C:5]1([S:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[CH2:6][C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:13]1)([OH:3])=[O:2]

Participants

6

Reactant 2

HCID 14797Potassium HydroxideHCID 152807342-(Carbomethoxy)-2-(4-methoxybenzylthio)indan

Product 1

HCID 152807352-Carboxy-2-(4-methoxybenzylthio)indanYield 43%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Dissolve 2-(carbomethoxy)-2-(4-methoxybenzylthio)indane (2.20 g, 3.55 mmol) in 95% ethanol (25 mL), water (12 mL) and tetrahydrofuran (15 mL). Treat with potassium hydroxide (1.3 g, 23 mmol) and stir at room temperature for 1 hour. Filter and evaporate the solvent in vacuo. Partition between water (125 mL) and ether (75 mL). Separate the aqueous phase and acidify with cold concentrated hydrochloric acid. Extract with methylene chloride (75 mL), dry (Na2SO4) and evaporate the solvent in vacuo. Purify by silica gel chromatography (2:1 hexane/ethyl acetate) to give 2-carboxy-2-(4-methoxybenzylthio)indane as a yellow solid (0.48 g, 43%).

Workup

  1. filtrationFilter
  2. customevaporate the solvent in vacuo
  3. customPartition between water (125 mL) and ether (75 mL)
  4. customSeparate the aqueous phase
  5. extractionExtract with methylene chloride (75 mL)
  6. dry with materialdry (Na2SO4)
  7. customevaporate the solvent in vacuo
  8. customPurify by silica gel chromatography (2:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-3b4f47a0a38e488e9137f155664cfb09
Source dataset
uspto-grants-1997_02
Patent number
US05604221

Reaction notes

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