Chloromethyl Methyl Ether → HCID 18461391, compound

HRID 2303846Notes

Reaction equation

HRID 2303846 reaction equation
[O:1]1[CH2:5]CC[CH2:2]1.[H-].[Na+].[CH3:8][C:9]1[CH:14]=[C:13]([O:15][C:16](=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18])[CH:12]=[C:11]([CH3:22])[C:10]=1[OH:23].COCCl>O>[C:16]([O:15][C:13]1[CH:12]=[C:11]([CH3:22])[C:10]([O:23][CH2:2][O:1][CH3:5])=[C:9]([CH3:8])[CH:14]=1)(=[O:21])[C:17]([CH3:19])([CH3:20])[CH3:18]

Participants

6

Reactant 4

HCID 7864Chloromethyl Methyl EtherHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 18461413HCID 18461413, compound

Product 1

HCID 18461391HCID 18461391, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 50 ml of an anhydrous tetrahydrofuran suspension containing 1.72 g of sodium hydride (55% by weight), 6.75 g of 2,6-dimethyl-4-pivaloyloxyphenol were added in small portions, followed by stirring at room temperature for 30 minutes. To the reaction mixture, 3.18 g of chloromethyl methyl ether were added and the resulting mixture was stirred at the same temperature for 3 hours. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The extract was dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure, whereby 8.17 g of 4-methoxymethoxy-3,5-dimethylphenyl pivaloate were obtained as a crude product.

Workup

  1. additionwere added in small portions
  2. stirringthe resulting mixture was stirred at the same temperature for 3 hours
  3. extractionfollowed by extraction with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-a5671e95f2944f979ff95054983f7b59
Source dataset
uspto-grants-2002_08
Patent number
US06432993B1

Reaction notes

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