Hydrochloric Acid → HCID 17819718, compound

HRID 1289276Notes

Reaction equation

HRID 1289276 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2(O)[CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH2:9]2)=[CH:4][CH:3]=1.Cl>C1COCC1.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH2:16][C:15]3[C:10]([CH:9]=2)=[CH:11][CH:12]=[CH:13][CH:14]=3)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 18690300HCID 18690300, compound

Product 1

HCID 17819718HCID 17819718, compoundYield 70.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(4-fluorophenyl)-2-indanol (21.0 g, 92.1 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 overnight (14 h). The solid was collected and washed with pentane (50 mL) and then tetrahydrofuran (50 mL) to give 13.7 g of yield 2-(4-fluorophenyl)-1H-indene. 1H-N.M.R. (CDCl3) d 3.78(br s, 2H), d 7.05 (br d, J=8.6 Hz, 2H), d 7.13(br s, 1H), d 7.17(tt, J=7.4, 1.2 Hz, 1H), d 7.7(br t J=7.4 Hz, 1H), d 7.38(br d, J=7.4Hz, 1H), d 7.45(br d, J=7.4 Hz, 1H), d 7.57(br dd, J=9.0, 5.4 Hz, 2H)

Workup

  1. customThe solid was collected
  2. washwashed with pentane (50 mL)

Sources & evidence

ORD record
ord-5d3da40f749f47939429b82f95b1b5e3
Source dataset
uspto-grants-1998_05
Patent number
US05747621

Reaction notes

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