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Chloromethyl Methyl Ether → 1-(3-Chloromethyl-4-methoxy-phenyl)-cyclopropanecarboxylic acid methyl ester

HRID 17909
Notes
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Reaction equation

HRID 17909 reaction equation
[CH3:1][O:2][C:3]([C:5]1([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)[CH2:7][CH2:6]1)=[O:4].[CH2:16]([Cl:19])OC>C(=S)=S.Cl[Ti](Cl)(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1([C:8]2[CH:9]=[CH:10][C:11]([O:14][CH3:15])=[C:12]([CH2:16][Cl:19])[CH:13]=2)[CH2:6][CH2:7]1)=[O:4]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 7864Chloromethyl Methyl EtherHCID 13707544Methyl 1-(4-methoxyphenyl)-cyclopropanecarboxylate

Product 1

HCID 591292541-(3-Chloromethyl-4-methoxy-phenyl)-cyclopropanecarboxylic acid methyl esterYield 102.2%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6348Carbon Disulfide
Solvent

Conditions

Temperature
30 °C

Procedure

To a solution of 1-(4-methoxy-phenyl)-cyclopropanecarboxylic acid methyl ester (30.0 g, 146 mmol) and MOMCl (29.1 g, 364 mmol) in CS2 (300 mL) was added TiCl4 (8.30 g, 43.5 mmol) at 5° C. The reaction mixture was heated at 30° C. for 1 day and poured into ice-water. The mixture was extracted with CH2Cl2 (150 mL×3). The combined organic extracts were evaporated under vacuum to give crude 1-(3-chloromethyl-4-methoxy-phenyl)-cyclopropanecarboxylic acid methyl ester (38.0 g), which was used in the next step without further purification.

Workup

  1. extractionThe mixture was extracted with CH2Cl2 (150 mL×3)
  2. customThe combined organic extracts were evaporated under vacuum

Sources & evidence

ORD record
ord-483bcf84b7d54dedbeeb1f829edeea94
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07741321B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes