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

HRID 1929955Notes

Reaction equation

HRID 1929955 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-carbaldehyde

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
  7. custom(m=40.7 g; yield =86%)

Sources & evidence

ORD record
ord-5236e3d7f764472f9d364794da529f75
Source dataset
uspto-grants-2012_05
Patent number
US08188106B2

Reaction notes

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