4-Fluorobenzaldehyde → (E)-6-(p-fluoro-alpha-methylstyryl)-1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalene

HRID 1608386Notes

Reaction equation

HRID 1608386 reaction equation
[Br-].[CH3:2][C:3]1([CH3:36])[CH2:12][CH2:11][C:10]([CH3:14])([CH3:13])[C:9]2[CH:8]=[C:7]([CH:15]([P+](C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH3:16])[CH:6]=[CH:5][C:4]1=2.[F:37][C:38]1[CH:45]=[CH:44][C:41]([CH:42]=O)=[CH:40][CH:39]=1.CO.O>C1OC1CC>[F:37][C:38]1[CH:45]=[CH:44][C:41](/[CH:42]=[C:15](/[C:7]2[CH:8]=[C:9]3[C:4](=[CH:5][CH:6]=2)[C:3]([CH3:36])([CH3:2])[CH2:12][CH2:11][C:10]3([CH3:13])[CH3:14])\[CH3:16])=[CH:40][CH:39]=1

Participants

5

Reactant 3

HCID 680234-FluorobenzaldehydeHCID 11238302Triphenyl(1-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)ethyl)phosphonium bromideHCID 22242641Methanol--water (1/1)

Product 1

HCID 14425578(E)-6-(p-fluoro-alpha-methylstyryl)-1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthaleneYield 53.9%

Reagents, catalysts & solvents 1

HCID 78341,2-EpoxybutaneSolvent

Procedure

45 g of [1-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-ethyl]-triphenylphosphonium bromide are suspended in 200 ml of 1,2-butylene oxide. After the addition of 8 g of 4-fluorobenzaldehyde the mixture is boiled at reflux for 16 hours. After cooling the clear, yellowish solution is poured into 1 l of methanol/water (6:4) and extracted repeatedly with hexane. The organic phase is washed three times with water and, after drying over sodium sulphate, evaporated. The crystalline residue can be recrystallized from hexane and gives 11.2 g of (E)-6-(p-fluoro-α-methylstyryl)-1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalene in colourless crystals, melting point 99°-101°.

Workup

  1. temperatureat reflux for 16 hours
  2. temperatureAfter cooling the clear, yellowish solution
  3. extractionextracted repeatedly with hexane
  4. washThe organic phase is washed three times with water
  5. dry with materialafter drying over sodium sulphate
  6. customevaporated
  7. customThe crystalline residue can be recrystallized from hexane

Sources & evidence

ORD record
ord-22176052a85b4e3198d568773396a5d8
Source dataset
uspto-grants-1989_09
Patent number
US04870219

Reaction notes

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