2-Chloroethyl methyl ether → 5,5,8,8-Tetramethyl-4-(2-methoxyethoxy)-5,6,7,8-tetrahydronaphthalene-2-carbaldehyde

HRID 498934Notes

Reaction equation

HRID 498934 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+].[CH3:20][O:21][CH2:22][CH2:23]Cl>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][CH2:23][CH2:22][O:21][CH3:20])[C:11]1=2

Participants

5

Reactant 3

HCID 123162-Chloroethyl methyl etherHCID 24758Sodium hydrideHCID 865995434-Hydroxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthalenecarbaldehyde

Product 1

HCID 866125925,5,8,8-Tetramethyl-4-(2-methoxyethoxy)-5,6,7,8-tetrahydronaphthalene-2-carbaldehydeYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

34 g (148 mmol) of 4-hydroxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-carbaldehyde are dissolved in 400 mL of anhydrous DMF. 7.2 g (178 mmol) of 60% sodium hydride are then added portionwise, and the reaction medium is stirred for 1 hour. 16.5 mL (178 mmol) of 2-methoxyethyl chloride are added dropwise, 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=42.7 g; yield=95%).

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=42.7 g; yield=95%)

Sources & evidence

ORD record
ord-367292b204d849cb936f20022e7c5fba
Source dataset
uspto-grants-2010_08
Patent number
US07767650B2

Reaction notes

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