Hydrochloric Acid → HCID 17903783, compound

HRID 1872302Notes

Reaction equation

HRID 1872302 reaction equation
[C:1]1([CH3:17])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1(O)[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8]1.Cl.C(OCC)C>C1COCC1.O>[C:1]1([CH3:17])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH2:15][C:14]2[C:9]([CH:8]=1)=[CH:10][CH:11]=[CH:12][CH:13]=2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 18690313HCID 18690313, compound

Product 1

HCID 17903783HCID 17903783, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(o-tolyl)-2-indanol (10.0 g, 44.6 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 (12 h). 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. Kugelrohr distillation yielded 5.8 g of 2-(o-tolyl)-1H-indene (150° C./0.3 mm Hg). 1H-N.M.R. (CDCl3) d 2.49(s, 3H), d 3.78 (d, J=0.90 Hz, 2H), d 6.94(br s, 1H), d 7.18-7.50(m, 8H).

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
  5. distillationKugelrohr distillation

Sources & evidence

ORD record
ord-0a6dff0c4290457e99fb5f11cdafce53
Source dataset
uspto-grants-2000_08
Patent number
US06107431

Reaction notes

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