Sulfuric Acid → HCID 11572310, compound

HRID 223122Notes

Reaction equation

HRID 223122 reaction equation
[CH:1]([CH:4]1[C:12]2[C:7](=[CH:8][C:9]([CH3:15])=[C:10]([Mg]Br)[CH:11]=2)[C:6]([CH3:17])([CH3:16])[CH:5]1[CH3:18])([CH3:3])[CH3:2].[Mg].BrC1C=C2C(C(C)(C)C(C)C2C(C)C)=CC=1C.S(=O)(=O)(O)O.CN(C)[CH:44]=[O:45]>>[CH:44]([C:10]1[CH:11]=[C:12]2[C:7]([C:6]([CH3:17])([CH3:16])[CH:5]([CH3:18])[CH:4]2[CH:1]([CH3:3])[CH3:2])=[CH:8][C:9]=1[CH3:15])=[O:45]

Participants

6

Reactant 5

HCID 1118Sulfuric AcidHCID 6228DimethylformamideHCID 5462224MagnesiumHCID 20522455HCID 20522455, compoundHCID 178421852HCID 178421852, compound

Product 1

HCID 11572310HCID 11572310, compound

Procedure

40 ml Bromine is added at 10° C. to a solution of 100 g 1-isopropyl-2,3,3,5-tetramethyl indan (obtained according to Example I or II) and 1 ml pyridine in 50 ml carbon tetrachloride. Then the reaction mixture is stirred during one hour and poured out into an aqueous solution of approximately 25 g sodium thiosulphate. The organic layer is separated, washed with 25% sodium hydroxide and evaporated. The residue is distilled under diminished pressure yielding 105 g 6-bromo-1-isopropyl-2,3,3,5-tetramethyl indan. B.p. 145°-150° C./1 mm Hg. 25 g Dimethyl formamide is added to a solution of 1-isopropyl-2,3,3,5-tetramethyl-6-indanyl magnesium bromide, prepared from 9 g magnesium and 100 g of the 6-bromo indan obtained above. The reaction mixture is then heated to reflux during 30 min., poured out into a mixture of ice and diluted sulphuric acid and extracted with ether. The solution in ether is washed neutral, dried and evaporated. The residue is distilled under diminished pressure yielding 30 g 6-formyl-1-isopropyl-2,3,3,5-tetramethyl indan. B.p. 135° C./1 mm Hg.

Workup

  1. customobtained above
  2. temperatureThe reaction mixture is then heated
  3. temperatureto reflux during 30 min.
  4. extractionextracted with ether
  5. washThe solution in ether is washed neutral
  6. customdried
  7. customevaporated
  8. distillationThe residue is distilled under diminished pressure

Sources & evidence

ORD record
ord-34a1c3a1232e4669b93460c7e1369b2a
Source dataset
uspto-grants-1982_10
Patent number
US04352748

Reaction notes

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