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

HRID 1616690Notes

Reaction equation

HRID 1616690 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-eea0e7475ec24e3b8b0ca7ab14fb2ea6
Source dataset
uspto-grants-2014_07
Patent number
US08765805B2

Reaction notes

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