Hexane → HCID 21221331, compound

HRID 1768643Notes

Reaction equation

HRID 1768643 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]=1

Participants

6

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

  1. stirringThe mixture was stirred for 30 min at 0° C
  2. filtrationthe mixture was filtered
  3. customto remove triphenylphosphineoxide
  4. washThe filtrate was washed with water
  5. dry with materiala saturated aqueous solution of sodium chloride, successively, dried over anhydrous magnesium sulfate
  6. customevaporated
  7. 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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