4-Methoxybenzaldehyde → 1,2,3,4-tetrahydro-6-[(E)-p-methoxy-alpha-methylstyryl]-1,1,4,4-tetramethylnaphthalene

HRID 359614Notes

Reaction equation

HRID 359614 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.C([Li])CCC.[CH3:42][O:43][C:44]1[CH:51]=[CH:50][C:47]([CH:48]=O)=[CH:46][CH:45]=1.CO.O>O1CCCC1>[CH3:42][O:43][C:44]1[CH:51]=[CH:50][C:47](/[CH:48]=[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:46][CH:45]=1

Participants

6

Reactant 4

HCID 312444-MethoxybenzaldehydeHCID 11238302Triphenyl(1-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)ethyl)phosphonium bromideHCID 22242641Methanol--water (1/1)HCID 178418339Butyllithium

Product 1

HCID 138854251,2,3,4-tetrahydro-6-[(E)-p-methoxy-alpha-methylstyryl]-1,1,4,4-tetramethylnaphthaleneYield 71.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

358 g of [1-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-ethyl]-triphenylphosphonium bromide are suspended in 600 ml of tetrahydrofuran and treated at 0° with 400 ml of n-butyllithium (1.6 molar in hexane). After stirring at 0° for 30 minutes a solution of 78.5 g of p-methoxybenzaldehyde in 200 ml of tetrahydrofuran is added dropwise thereto and the mixture is stirred at room temperature for a further 2 hours. The reaction mixture is subsequently poured into 2 l of methanol/water (6:4) and extracted repeatedly with hexane. The organic phase is washed three times with water and, after drying with sodium sulphate, evaporated. The crystalline residue can be recrystallized from hexane and gives 138 g of 1,2,3,4-tetrahydro-6-[(E)-p-methoxy-α-methylstyryl]-1,1,4,4-tetramethylnaphthalene, melting point 108°-110°.

Workup

  1. additionis added dropwise
  2. extractionextracted repeatedly with hexane
  3. washThe organic phase is washed three times with water
  4. dry with materialafter drying with sodium sulphate
  5. customevaporated
  6. customThe crystalline residue can be recrystallized from hexane

Sources & evidence

ORD record
ord-f724df0abc2a4b0dbd99d45e2f25d70c
Source dataset
uspto-grants-1991_03
Patent number
US05001276

Reaction notes

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