Sodium hydride → 5,5,8,8-Tetramethyl-4-(2-ethoxyethoxy)-5,6,7,8-tetrahydronaphthalene-2-carbaldehyde

HRID 498935Notes

Reaction equation

HRID 498935 reaction equation
[OH:1][C:2]1[C:11]2[C:10]([CH3:13])([CH3:12])[CH2:9][CH2:8][C:7]([CH3:15])([CH3:14])[C:6]=2[CH:5]=[C:4]([CH:16]=[O:17])[CH:3]=1.[H-].[Na+].[CH2:20]([O:22][CH2:23][CH2:24]Br)[CH3:21]>CN(C=O)C>[CH3:13][C:10]1([CH3:12])[CH2:9][CH2:8][C:7]([CH3:15])([CH3:14])[C:6]2[CH:5]=[C:4]([CH:16]=[O:17])[CH:3]=[C:2]([O:1][CH2:21][CH2:20][O:22][CH2:23][CH3:24])[C:11]1=2

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 611412-Bromoethyl ethyl etherHCID 865995434-Hydroxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthalenecarbaldehyde

Product 1

HCID 866125935,5,8,8-Tetramethyl-4-(2-ethoxyethoxy)-5,6,7,8-tetrahydronaphthalene-2-carbaldehydeYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

36 g (156 mmol) of 4-hydroxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-carbaldehyde are dissolved in 400 mL of anhydrous DMF. 6.5 g (163 mmol) of 60% sodium hydride are added portionwise and the reaction medium is stirred for 1 hour. 25 g (163 mmol) of 2-ethoxyethyl bromide are added portionwise and the medium is stirred at room temperature for 2 hours and then hydrolysed and extracted with ethyl ether. The organic phase is washed with 1N sodium hydroxide solution, and then three times with water. The residue obtained is purified by chromatography (eluent:heptane). A yellow oil is obtained (m=40.7 g; yield=86%).

Workup

  1. stirringthe medium is stirred at room temperature for 2 hours
  2. extractionhydrolysed and extracted with ethyl ether
  3. washThe organic phase is washed with 1N sodium hydroxide solution
  4. customThe residue obtained
  5. customis purified by chromatography (eluent:heptane)
  6. customA yellow oil is obtained (m=40.7 g; yield=86%)

Sources & evidence

ORD record
ord-0f236feb1bac4a3987349ec056c8ecf7
Source dataset
uspto-grants-2010_08
Patent number
US07767650B2

Reaction notes

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