Chloromethyl Methyl Ether → HCID 53991562, compound

HRID 637325Notes

Reaction equation

HRID 637325 reaction equation
[H-].[Li+].[CH3:3][C:4]1([CH3:12])[C@H:6]([CH:7]=[O:8])[C@H:5]1[C:9]([OH:11])=[O:10].[CH3:13][O:14][CH2:15]Cl.C(=O)(O)[O-].[Na+]>O.O1CCCC1>[CH3:3][C:4]1([CH3:12])[C@H:6]([CH:7]=[O:8])[C@H:5]1[C:9]([O:11][CH2:13][O:14][CH3:15])=[O:10]

Participants

7

Reactant 4

HCID 7864Chloromethyl Methyl EtherHCID 62714Lithium hydrideHCID 516892Sodium BicarbonateHCID 12919118Cyclopropanecarboxylic acid, 3-formyl-2,2-dimethyl-, (1R-trans)-

Product 1

HCID 53991562HCID 53991562, compoundYield 45.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
15 °C

Procedure

A mixture of 1.64 g of lithium hydride and 25.6 g of (1R,trans) 2,2-dimethyl-3-formyl-cyclopropane-carboxylic acid and 25 ml of tetrahydrofuran was stirred at 15° C. for 30 minutes and then 18.2 g of a freshly prepared chloromethyl methyl ether (0.225 mols) were added thereto. The mixture was stirred at 20° C. for 4 hours and was then poured into a mixture of ice, water and sodium bicarbonate with stirring. The mixture was extracted with isopropyl ether and the organic phase was evaporated to dryness under reduced pressure. The residue was rectified under vacuum to obtain 15.15 g of methoxymethyl (1R,trans) 2,2-dimethyl-3-formyl-cyclopropane-carboxylate with a boiling point of 67° C. at 0.05 mm Hg.

Workup

  1. stirringThe mixture was stirred at 20° C. for 4 hours
  2. stirringwith stirring
  3. extractionThe mixture was extracted with isopropyl ether
  4. customthe organic phase was evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-f727421f4ed148d2b30f4fd2c1123eff
Source dataset
uspto-grants-1985_12
Patent number
US04556666

Reaction notes

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