Hydrochloric Acid → 1-(1,2,3,4-Tetrahydro-4,4-dimethyl-1-naphthalenyl)-1-propanone

HRID 1995880Notes

Reaction equation

HRID 1995880 reaction equation
[CH3:1][C:2]1([CH3:14])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]([C:12]#N)[CH2:4][CH2:3]1.[Mg].[CH2:16](Br)[CH3:17].Cl.CC[O:22]CC>>[CH3:1][C:2]1([CH3:14])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]([C:12](=[O:22])[CH2:16][CH3:17])[CH2:4][CH2:3]1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 3283Diethyl Ether2×HCID 6332Ethyl BromideHCID 1741091-Naphthalenecarbonitrile, 1,2,3,4-tetrahydro-4,4-dimethyl-HCID 5462224Magnesium

Product 1

HCID 1664451-(1,2,3,4-Tetrahydro-4,4-dimethyl-1-naphthalenyl)-1-propanoneYield 55%

Procedure

61.8 g of 1,1-dimethyl-4-cyano-tetralin in 100 ml of absolute ether are added dropwise while stirring to a Grignard solution prepared from 600 ml of ether, 34.7 g of magnesium shavings and 166 g of ethyl bromide. The mixture is held at reflux temperature for 6 hours, cooled and acidified with 10% hydrochloric acid. The aqueous phase is separated as rapidly as possible and held at reflux temperature for 1 hour. It is cooled, extracted with ether, washed neutral with water, dried over sodium sulphate and evaporated. Distillation in vacuo gives 39.4 g of 1,1-dimethyl-4-propionyl-tetralin of boiling point 75° C./0.05 mmHg; nD20 =1.5263; yield 55%. Odour: rose note, tobacco-like (light), dried fruits, berries, damascone, honey.

Workup

  1. temperatureat reflux temperature for 6 hours
  2. temperaturecooled
  3. customThe aqueous phase is separated as rapidly as possible and
  4. temperatureat reflux temperature for 1 hour
  5. temperatureIt is cooled
  6. extractionextracted with ether
  7. washwashed neutral with water
  8. dry with materialdried over sodium sulphate
  9. customevaporated
  10. distillationDistillation in vacuo

Sources & evidence

ORD record
ord-b563b6655e4b4b0e8e030e2b2972b58a
Source dataset
uspto-grants-1983_09
Patent number
US04406828

Reaction notes

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