Methyl chloroacetate → HCID 86623835, compound

HRID 1710323Notes

Reaction equation

[CH3:1][O:2][C:3]([CH3:12])([CH2:10][CH3:11])[CH2:4][CH2:5][CH2:6][C:7](=[O:9])[CH3:8].COC(C)(C)C.Cl[CH2:20][C:21]([O:23][CH3:24])=[O:22].C[O-].[Na+]>C(O)(=O)C>[CH3:24][O:23][C:21]([CH:20]1[C:7]([CH2:6][CH2:5][CH2:4][C:3]([O:2][CH3:1])([CH3:12])[CH2:10][CH3:11])([CH3:8])[O:9]1)=[O:22]

Participants

Conditions

Temperature: 0 °C

Procedure

860 g 6-Methoxy-6-methyl-2-octanone, 4 l tert.-butyl methyl ether and 648 g methyl chloroacetate were cooled to 0° C. under a blanket of nitrogen. Under further cooling, 350 g sodium methoxide was added in 6 portions over 20 minutes. The mixture was then stirred at room temperature till no more consumption of the ketone was observed (GC). After cooling to 0° C., 1 l 5% acetic acid (w/w) was added and the phases were separated. The aqueous phase was extracted with tert.-butyl methyl ether (500 ml). The combined organic phases were washed with water, concentrated KHCO3 solution, concentrated NaCl solution and dried over MgSO4. The yellow oil which remained after the removal of the solvent was distilled over a small Vigreux-column to give 823 g of 3-(4-methoxy-4-methyl-hexyl)-3-methyl-oxirane-2-carboxylic acid methyl ester (mixture of isomers, boiling point: 115°-128°/0.3 Torr=0.399 mbar).

Workup

customthe phases were separated
extractionThe aqueous phase was extracted with tert.-butyl methyl ether (500 ml)
washThe combined organic phases were washed with water, concentrated KHCO3 solution, concentrated NaCl solution
dry with materialdried over MgSO4
customafter the removal of the solvent
distillationwas distilled over a small Vigreux-column

Sources & evidence

ORD record: ord-08294551164d48f9963c6aecd27a7540
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07790668B2

Reaction notes

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