Trimethyl orthoformate → HCID 68449830, compound

HRID 1297551Notes

Reaction equation

HRID 1297551 reaction equation
[CH3:1]/[C:2](=[CH:5]\[C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=1)/[CH:3]=[O:4].[CH:13](OC)(OC)OC>ClCCl.C(OCC)C>[CH3:13][O:4][CH:3]1[C:7]2[C:6](=[CH:11][CH:10]=[C:9]([CH3:12])[CH:8]=2)[CH:5]=[C:2]1[CH3:1]

Participants

5

Reactant 2

HCID 9005Trimethyl orthoformateHCID 11984401HCID 11984401, compound

Product 1

HCID 68449830HCID 68449830, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

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 trimethyl orthoformate (36.4 g, 34.3 mmol.) in dichloromethane (35 ml). The dark red solution was stirred for one hour, 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 (65-80° C., 20 mTorr) yielded 3.2 g (18.4 mmol., 59% 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 (65-80° C., 20 mTorr)

Sources & evidence

ORD record
ord-799300e120104e92b4889365de9a8fa1
Source dataset
uspto-grants-2007_07
Patent number
US07250528B2

Reaction notes

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