2-Nitropropane → 3-Bromo-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-carbaldehyde

HRID 1836878Notes

Reaction equation

HRID 1836878 reaction equation
[Na].[N+](C(C)C)([O-])=[O:3].[Br:8][C:9]1[C:18]([CH2:19]Br)=[CH:17][C:16]2[C:15]([CH3:22])([CH3:21])[CH2:14][CH2:13][C:12]([CH3:24])([CH3:23])[C:11]=2[CH:10]=1>C(O)C>[Br:8][C:9]1[C:18]([CH:19]=[O:3])=[CH:17][C:16]2[C:15]([CH3:22])([CH3:21])[CH2:14][CH2:13][C:12]([CH3:24])([CH3:23])[C:11]=2[CH:10]=1

Participants

5

Reactant 3

HCID 3982-NitropropaneHCID 5360545SodiumHCID 234989536-Bromo-7-(bromomethyl)-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 177898873-Bromo-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-carbaldehydeYield 61%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

0.981 g (42.7 mmol) of sodium was dissolved in 50 mL of ethanol. To this solution was added 4.94 g (55.5 mmol) of 2-nitropropane followed by 17.3 g (42.7 mmol) of crude 2-bromo-3-bromomethyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene in 75 mL ethanol. After 8 hours, this mixture was concentrated in vacuo and then partitioned between ethyl acetate and water. The organic layer was sequentially washed with 1M aqueous sodium hydroxide, water, brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The product was purified by flash chromatography on silica gel with gradient elution (1-2% ethyl acetate/hexane) to afford 7.63 g (61%) of 3-bromo-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthaldehyde (m.p.=113.9-114.3° C.).

Workup

  1. concentrationthis mixture was concentrated in vacuo
  2. custompartitioned between ethyl acetate and water
  3. washThe organic layer was sequentially washed with 1M aqueous sodium hydroxide, water, brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe product was purified by flash chromatography on silica gel with gradient elution (1-2% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-2af467902f154c71b5c884f5c0714369
Source dataset
uspto-grants-2004_08
Patent number
US06777418B2

Reaction notes

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