Sodium hydride → 2-Methyl-5-(2-(trimethylsilyl)ethoxymethoxy)benzaldehyde

HRID 322978Notes

Reaction equation

HRID 322978 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].[H-].[Na+].[CH3:13][Si:14]([CH3:21])([CH3:20])[CH2:15][CH2:16][O:17][CH2:18]Cl>>[CH3:10][C:5]1[CH:4]=[CH:3][C:2]([O:1][CH2:18][O:17][CH2:16][CH2:15][Si:14]([CH3:21])([CH3:20])[CH3:13])=[CH:9][C:6]=1[CH:7]=[O:8]

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 5858755-Hydroxy-2-methylbenzaldehydeHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl ether

Product 1

HCID 220104442-Methyl-5-(2-(trimethylsilyl)ethoxymethoxy)benzaldehydeYield 103.3%

Procedure

5-hydroxy-2-methylbenzaldehyde (3.4 g) is added portionwise to a stirred suspension of sodium hydride (1.2 g, 60% dispersion in mineral oil). The reaction mixture is stirred at room temperature for 45 minutes, 2-(trimethylsilyl)ethoxymethyl chloride (5 g) is added slowly and stirring continued for a further 3 hours. The mixture is evaporated and the residue partitioned between ethyl acetate (50 mL) and water (150 mL). The organic phase is washed with brine (150 mL) dried over magnesium sulphate and evaporated to give 2-methyl-5-(2-(trimethylsilyl)ethoxymethoxy)benzaldehyde (6.87 g) as a red-brown oil.

Workup

  1. stirringstirring
  2. waitcontinued for a further 3 hours
  3. customThe mixture is evaporated
  4. customthe residue partitioned between ethyl acetate (50 mL) and water (150 mL)
  5. washThe organic phase is washed with brine (150 mL)
  6. dry with materialdried over magnesium sulphate
  7. customevaporated

Sources & evidence

ORD record
ord-bef07d2b69304082860c6aab2ee987ee
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Reaction notes

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