2-(Phenylmethylene)octanal → 1,3-Diphenyl-2-n-hexyl-2-propen-1-ol

HRID 1377227

Reaction equation

HRID 1377227 reaction equation
[Mg].[Br-].[CH:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:9]([C:15](=[CH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH:16]=[O:17])[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]>O1CCCC1>[C:3]1([CH:16]([OH:17])[C:15]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=[CH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 75852-(Phenylmethylene)octanalHCID 5462224MagnesiumHCID 22259850Benzene bromide

Product 1

HCID 539411361,3-Diphenyl-2-n-hexyl-2-propen-1-olYield 115.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In a 2-liter three-necked flask equipped with a stirring device, a thermometer and a nitrogen substituting device, 13.2 g of magnesium and 300 milliliters of tetrahydrofuran were introduced and stirred violently. Then, a solution of 83.2 g of benzene bromide in 100 milliliters of tetrahydrofuran was added dropwise for 40 minutes. At that time, cooling was carried out with an ice bath if required. After the dropwise addition was ended, stirring was carried out at room temperature for 1 hour, and thereafter 108.2 g of α-n-hexyl cinnamaldehyde was added dropwise. After stirring for one day and one night, the solution was poured in ice water containing dilute hydrochloric acid, and extracted with 1 liter of ethyl acetate. After the solution was washed with an aqueous solution of sodium hydrogencarbonate and water, it was dried with anhydrous magnesium sulfate. After removing the solvent off by a rotary evaporator, 169.6 g of 1,3-diphenyl-2-n-hexyl-2-propen-1-ol was obtained.

Workup

  1. customIn a 2-liter three-necked flask equipped with a stirring device
  2. temperatureAt that time, cooling
  3. customwas carried out with an ice bath
  4. additionAfter the dropwise addition
  5. stirringstirring
  6. stirringAfter stirring for one day and one night
  7. extractionextracted with 1 liter of ethyl acetate
  8. washAfter the solution was washed with an aqueous solution of sodium hydrogencarbonate and water, it
  9. dry with materialwas dried with anhydrous magnesium sulfate
  10. customAfter removing the solvent
  11. customoff by a rotary evaporator

Sources & evidence

ORD record
ord-cf43499f97234150b816bd638d1d0805
Source dataset
uspto-grants-1997_09
Patent number
US05663440

Linked notes

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