Benzyl Chloride → HCID 86743409, compound

HRID 1608390Notes

Reaction equation

HRID 1608390 reaction equation
[CH2:1]([C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[C:11]([CH3:16])([CH3:15])[CH2:10][CH2:9][C:8]2([CH3:18])[CH3:17])=O)[CH3:2].[CH2:19]([Mg]Cl)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[Mg].C(Cl)C1C=CC=CC=1.[Cl-].[NH4+]>CCOCC>[CH2:1]([C:3]([C:5]1[CH2:6][CH:7]2[C:12](=[CH:13][CH:14]=1)[C:11]([CH3:16])([CH3:15])[CH2:10][CH2:9][C:8]2([CH3:18])[CH3:17])=[CH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH3:2]

Participants

7

Reactant 5

HCID 7503Benzyl ChlorideHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 45271609HCID 45271609, compoundHCID 178418336HCID 178418336, compound

Product 1

HCID 86743409HCID 86743409, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

6.1 g of (1,2,3,4-tetrahydro-1,1,4,4-tetramethyl-6-naphthyl) ethyl ketone are dissolved in 25 ml of abs. ether and added dropwise at 0° to a benzylmagnesium chloride solution prepared from 0.6 g of magnesium and 4.3 g of benzyl chloride in 30 ml of abs. ether. After stirring at room temperature for 2 hours the reaction mixture is poured into a saturated ammonium chloride solution, extracted with ether, dried over sodium sulphate and evaporated. The thus-obtained oil is dissolved in 100 ml of toluene and, after the addition of 0.5 g of p-toluenesulphonic acid, boiled at reflux overnight. After cooling the mixture is treated with 10% sodium bicarbonate solution, extracted with ether, dried and evaporated. The residue is purified by filtration over a short column (silica gel, elution agent hexane) and recrystallized from methylene chloride/methanol. There are obtained 3 g of 6-(α-ethylstyryl)-1,2,3,5-tetrahydro-1,1,4,4-tetramethylnaphthalene in colourless crystals, melting point 65°.

Workup

  1. extractionextracted with ether
  2. dry with materialdried over sodium sulphate
  3. customevaporated
  4. dissolutionThe thus-obtained oil is dissolved in 100 ml of toluene
  5. additionafter the addition of 0.5 g of p-toluenesulphonic acid
  6. temperatureat reflux overnight
  7. temperatureAfter cooling the mixture
  8. additionis treated with 10% sodium bicarbonate solution
  9. extractionextracted with ether
  10. customdried
  11. customevaporated
  12. filtrationThe residue is purified by filtration over a short column (silica gel, elution agent hexane)
  13. customrecrystallized from methylene chloride/methanol

Sources & evidence

ORD record
ord-575a7d183e7e489ba1ea459c95d769f9
Source dataset
uspto-grants-1989_09
Patent number
US04870219

Reaction notes

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