Ethyl Bromide → 1-(1,2,3,4-Tetrahydro-4,4-dimethyl-1-naphthalenyl)-1-propanone

HRID 1995884Notes

Reaction equation

HRID 1995884 reaction equation
[CH3:1][C:2]1([CH3:15])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]([C:12](Cl)=[O:13])[CH2:4][CH2:3]1.[Mg].[CH2:17](Br)[CH3:18]>CCOCC.[Cu]I>[CH3:1][C:2]1([CH3:15])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]([C:12](=[O:13])[CH2:17][CH3:18])[CH2:4][CH2:3]1

Participants

6

Reactant 3

HCID 6332Ethyl BromideHCID 5462224MagnesiumHCID 54561769HCID 54561769, compound

Product 1

HCID 1664451-(1,2,3,4-Tetrahydro-4,4-dimethyl-1-naphthalenyl)-1-propanoneYield 64%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 3283Diethyl EtherSolvent2×

Procedure

223 g (1 mol) of 1,1-dimethyl-tetralin-4-carboxylic acid chloride and 11 g of copper (I) iodide are placed in a 1-liter flask provided with a thermometer, stirrer, dropping funnel and reflux condenser and there is allowed to drop in from the dropping funnel at -10° C. to -5° C. a Grignard solution freshly prepared from 27 g (1.1 mol) of magnesium shavings and 122 (1.12 mol) of ethyl bromide in 500 ml of absolute ether. In so doing, the mixture must be diluted with a small amount of ether. The mixture is stirred for a further 5 hours while cooling and then the cooling source is removed. After the mixture has reached room temperature, it is poured into cold, saturated ammonium chloride solution, extracted with ether, washed neutral with water, dried over sodium sulphate and evaporated. Fractional distillation gives 138 g of 1,1-dimethyl-4-propionyl-tetralin of boiling point 75° C./0.05 mmHg; nD20 =1.5263; yield 64%. Ventilation can further improve the olfactory quality. Odour: see (3).

Workup

  1. customprovided with a thermometer, stirrer
  2. temperaturereflux condenser
  3. customto drop in from the dropping funnel at -10° C. to -5° C.
  4. temperaturewhile cooling
  5. customthe cooling source is removed
  6. customhas reached room temperature
  7. additionit is poured into cold, saturated ammonium chloride solution
  8. extractionextracted with ether
  9. washwashed neutral with water
  10. dry with materialdried over sodium sulphate
  11. customevaporated
  12. distillationFractional distillation

Sources & evidence

ORD record
ord-e6c061b8fe3f445b8123e6d53e9b9c56
Source dataset
uspto-grants-1983_09
Patent number
US04406828

Reaction notes

Loading…