Hexane → HCID 21221331, compound
Reaction equation
[C:1]([Br:5])(Br)(Br)[Br:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH:25]([CH2:27][CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([O:36][CH3:37])[CH:31]=1)=O.CCCCCC>C(Cl)Cl>[Br:2][C:1]([Br:5])=[CH:25][CH2:27][CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([O:36][CH3:37])[CH:31]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of carbon tetrabromide (16.7 g)in methylene chloride (35 ml) was added triphenyiphosphine (26.0 g) in methylene chloride (35 ml) at 0° C. and the mixture was stirred for 10 min. To the mixture was added a solution of 1-(3-formylpropyl)-3-methoxybenzene (3.00 g) in methylene chloride (20 ml) at 0° C. The mixture was stirred for 30 min at 0° C. To the mixture was added gradually n-hexane and the mixture was filtered to remove triphenylphosphineoxide. The filtrate was washed with water and a saturated aqueous solution of sodium chloride, successively, dried over anhydrous magnesium sulfate and evaporated. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=24:1) to give the title compound (5.33 g) having the following physical data.
Workup
- stirringThe mixture was stirred for 30 min at 0° C
- filtrationthe mixture was filtered
- customto remove triphenylphosphineoxide
- washThe filtrate was washed with water
- dry with materiala saturated aqueous solution of sodium chloride, successively, dried over anhydrous magnesium sulfate
- customevaporated
- customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=24:1)
Sources & evidence
- ORD record
- ord-a07a1e1117fb416dbc241761cadc5863
- Source dataset
- uspto-grants-1995_01
- Patent number
- US05378716
Reaction notes
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