Hydrochloric Acid → 2-Phenyl-1H-indene

HRID 1872293Notes

Reaction equation

HRID 1872293 reaction equation
[C:1]1([C:7]2(O)[CH2:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.C(OCC)C>C1COCC1.O>[C:1]1([C:7]2[CH2:15][C:14]3[C:9]([CH:8]=2)=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 14449200HCID 14449200, compound

Product 1

HCID 3534352-Phenyl-1H-indeneYield 92%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-phenyl-2-hydroxy-2,3-dihydro-1H-indene (6.88 g, 32.76 mmol) in THF (200 mL) was added a solution of concentrated hydrochloric acid (40 mL) in water (60 mL). The solution was stirred at room temperature for 3 day. Diethyl ether (200 mL) and water added. Aqueous layer was extracted with diethyl ether (3*200 mL). All etheral layers were combined, washed with water (50 mL), brine (50 mL), dried over anhydrous magnesium sulphate, and concentrated to yield 5.60 g (92%) of 2-phenyl-1H-indene. 1H-N.M.R. (CDCl3) d 3.78 (t, J=0.8 Hz, 2H), d 7.18-7.48(m, 8H), d 7.63(br d, J=7.1 Hz, 2H).

Workup

  1. extractionAqueous layer was extracted with diethyl ether (3*200 mL)
  2. washwashed with water (50 mL), brine (50 mL)
  3. dry with materialdried over anhydrous magnesium sulphate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d38bef7f8a1b45e9b80d997b32b03862
Source dataset
uspto-grants-2000_08
Patent number
US06107431

Reaction notes

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