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Chloromethyl Methyl Ether → Diethyl 4-(methoxymethoxy)cyclohexane-1,1-dicarboxylate

HRID 1059298
Notes
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Reaction equation

HRID 1059298 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][C:5]([C:13]([O:15][CH2:16][CH3:17])=[O:14])([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]1.C(N(C(C)C)CC)(C)C.[CH3:27][O:28][CH2:29]Cl>ClCCl>[CH3:27][O:28][CH2:29][O:1][CH:2]1[CH2:3][CH2:4][C:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:6][CH2:7]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 18670742Diethyl 4-hydroxycyclohexane-1,1-dicarboxylate

Product 1

HCID 18670551Diethyl 4-(methoxymethoxy)cyclohexane-1,1-dicarboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

12.3 g of diethyl 4-hydroxycyclohexane-1,1-dicarboxylate was dissolved in 160 ml of dichloromethane and 26.3 ml of diisopropylethylamine was added thereto followed by ice-cooling. Next, 9.6 ml of chloromethyl methyl ether was added thereto and the reaction mixture was stirred at room temperature for 15 hours. Then the reaction mixture was concentrated and the residue was purified by silica gel column chromatography (eluted with n-hexane/ethyl acetate) to thereby give 11.10 g of the title compound as a colorless oily substance.

Workup

  1. temperaturecooling
  2. concentrationThen the reaction mixture was concentrated
  3. customthe residue was purified by silica gel column chromatography (eluted with n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-273b8bc3c26841ec8ebd62a662593a6d
Source dataset
uspto-grants-2003_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06518423B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes