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

HRID 345211Notes

Reaction equation

HRID 345211 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-13d480ed84ca4c59adc8f6420fa315d5
Source dataset
uspto-grants-1991_10
Patent number
US05055622

Reaction notes

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