Benzaldehyde, 4-octyl- → HCID 57554608, compound

HRID 1511892Notes

Reaction equation

HRID 1511892 reaction equation
[CH2:1]([C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[CH2:17]([Mg]Br)[CH:18]=[CH2:19]>C1COCC1>[CH2:1]([C:9]1[CH:10]=[CH:11][C:12]([CH:13]([OH:14])[CH2:19][CH:18]=[CH2:17])=[CH:15][CH:16]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

4

Reactant 2

HCID 2734685Benzaldehyde, 4-octyl-HCID 178455850HCID 178455850, compound

Product 1

HCID 57554608HCID 57554608, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
2.5 °C

Procedure

4-octylbenzaldehyde (10.0 g, 45.8 mmol) (Aldrich) was dissolved in THF (229 ml) under nitrogen. The reaction was cooled to about 0-5° C. in an ice bath. A solution of allylmagnesium bromide (48.1 ml, 48.1 mmol) (Aldrich) was added slowly and the reaction stirred for about 2 h. The reaction was quenched by the addition of saturated ammonium chloride followed by addition of ethyl acetate. The layers were separated and the aqueous extracted with ethyl acetate. The combined extracts were washed with brine, dried over sodium sulfate, filtered, and evaporated to an off-white oil. The residue was dissolved in ether and dried over sodium sulfate and filtered. The solvents were removed under reduced pressure to provide 1-(4-octylphenyl)but-3-en-1-ol (11.54 g, 44.3 mmol, 97% yield) as a light yellow oil: LC/MS (method f) Rt=2.90 min.; MS m/z: 243.21 (M-water)+.

Workup

  1. customThe reaction was quenched by the addition of saturated ammonium chloride
  2. additionfollowed by addition of ethyl acetate
  3. customThe layers were separated
  4. extractionthe aqueous extracted with ethyl acetate
  5. washThe combined extracts were washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated to an off-white oil
  9. dissolutionThe residue was dissolved in ether
  10. dry with materialdried over sodium sulfate
  11. filtrationfiltered
  12. customThe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-945db725322a4f5da6c8b2506e95dc46
Source dataset
uspto-grants-2012_07
Patent number
US08217027B2

Reaction notes

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