p-Toluenesulfonic acid → 5-Methoxy-1H-indene

HRID 501697Notes

Reaction equation

HRID 501697 reaction equation
C[C:2]1(O)[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:11][CH3:12])[CH:9]=2)[CH2:4][CH2:3]1.CC1C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH3:12][O:11][C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[CH2:4][CH:3]=[CH:2]2

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 68465496methyl 6-methoxy-2,3-dihydro-1H-inden-1-ol

Product 1

HCID 127219015-Methoxy-1H-indene

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
90 °C

Procedure

Step AA (2): To a solution of crude methyl 6-methoxy-2,3-dihydro-1H-inden-1-ol from Step AA (1) (24.3 g) in benzene (100 mL) was added pTSA (250 mg), and the resulting solution was heated at 90° C. for 3 h with a Dean-Stark trap to remove water. Saturated sodium bicarbonate was added, the aqueous layer was extracted with EtOAc (×3), and the combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered, and evaporated. The crude product was distilled under vacuum to provide 5-methoxy-1H-indene as a colorless liquid (10 g). 1H NMR (400 MHz, CDCl3): 7.33 (1H, d), 6.96 (1H, d), 6.81 (1H, m), 6.75 (1H, m), 6.56 (1H, m), 3.82 (3H, s), 3.33 (2H, m).

Workup

  1. customto remove water
  2. additionSaturated sodium bicarbonate was added
  3. extractionthe aqueous layer was extracted with EtOAc (×3)
  4. washthe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. distillationThe crude product was distilled under vacuum

Sources & evidence

ORD record
ord-5a5f9b0b92094131829107d216aaa543
Source dataset
uspto-grants-2010_08
Patent number
US07772221B2

Reaction notes

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