Dichloromethane → 1-ethoxy-2,6-dimethyl-1H-indene

HRID 1297550Notes

Reaction equation

HRID 1297550 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[CH2:11])C=O)=[CH:4][CH:3]=1.[CH:12](OCC)(OCC)[O:13][CH2:14][CH3:15].Cl[CH2:23]Cl>C(OCC)C>[CH2:14]([O:13][CH:12]1[C:4]2[C:5](=[CH:6][CH:7]=[C:2]([CH3:1])[CH:3]=2)[CH:8]=[C:11]1[CH3:23])[CH3:15]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 31214Ethyl orthoformateHCID 180009044-Methylphenyl-2-propenal

Product 1

HCID 684460141-ethoxy-2,6-dimethyl-1H-indeneYield 24%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Anhydrous FeCl3 (2.0 g, 12.3 mmol.) was added to a solution of (2E)-2-methyl-3-(4-methylphenyl-2-propenal (5.0 g, 31.3 mmol.) and triethyl orthoformate (5.1 g, 34.5 mmol.) in dichloromethane (35 ml). The dark red solution was stirred at room temperature for 1 day, then diluted with 100 ml of diethyl ether and washed with water (3×75 ml). The organic phase was dried (MgSO4), filtered and concentrated. Kugelrohr distillation (54° C., 20 mTorr) yielded 1.4 g (7.4 mmol., 24% yield) of the title compound.

Workup

  1. washwashed with water (3×75 ml)
  2. dry with materialThe organic phase was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. distillationKugelrohr distillation (54° C., 20 mTorr)

Sources & evidence

ORD record
ord-29c1d6f93bec4a608cc7e920b83e18fc
Source dataset
uspto-grants-2007_07
Patent number
US07250528B2

Reaction notes

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