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

HRID 1979511Notes

Reaction equation

HRID 1979511 reaction equation
P(=O)(O)(O)O.[CH3:6][C:7](=[CH:9][CH2:10][CH:11]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:12](=[O:15])[CH2:13][CH3:14])[CH3:8]>C1(C)C=CC=CC=1>[CH3:6][C:7]1([CH3:8])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:11]([C:12](=[O:15])[CH2:13][CH3:14])[CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 1004Phosphoric AcidHCID 20439306HCID 20439306, compound

Product 1

HCID 1664451-(1,2,3,4-Tetrahydro-4,4-dimethyl-1-naphthalenyl)-1-propanoneYield 70%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

36 g of 85% phosphoric acid, 36 g of polyphosphoric acid, 175 ml of toluene and 72 g of 2-methyl-5phenyl-oct-2-en-6-one are heated together at 100° C. for 2 hours under a nitrogen atmosphere and while stirring. The mixture is left to cool, 250 ml of ice/water are added, the aqueous phase is separated and the organic phase is subjected to a steam distillation. The distillate is separated from the water and distilled in vacuo. There are obtained 50 g of 1,1-dimethyl-4-propionyl-tetralin of boiling point 75° C./0.05 mmHg; nD20 =1.5263; yield 70%. Odour: see (3).

Workup

  1. waitThe mixture is left
  2. temperatureto cool
  3. customthe aqueous phase is separated
  4. distillationthe organic phase is subjected to a steam distillation
  5. customThe distillate is separated from the water
  6. distillationdistilled in vacuo

Sources & evidence

ORD record
ord-8c415be7cba04e2c80fa1e5983de183c
Source dataset
uspto-grants-1984_11
Patent number
US04481133

Reaction notes

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