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Diethyl Ether → 4-Methoxymethylbezyl 2,2-dimethyl-3-(3-methoxy-3-oxo-1-propenyl)cyclopropanecarboxylate

HRID 1872078
Notes
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Reaction equation

HRID 1872078 reaction equation
[CH3:1][C:2]1([CH3:14])[CH:4]([CH:5]=[CH:6][C:7]([O:9][CH3:10])=[O:8])[CH:3]1[C:11]([OH:13])=[O:12].[CH3:15][O:16][CH2:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22]Br)=[CH:20][CH:19]=1.C(N(CC)CC)C.CCOCC>CC(C)=O>[CH3:1][C:2]1([CH3:14])[CH:4]([CH:5]=[CH:6][C:7]([O:9][CH3:10])=[O:8])[CH:3]1[C:11]([O:13][CH2:22][C:21]1[CH:24]=[CH:25][C:18]([CH2:17][O:16][CH3:15])=[CH:19][CH:20]=1)=[O:12]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 112643741-(Bromomethyl)-4-(methoxymethyl)benzeneHCID 545573312,2-Dimethyl-3-(3-methoxy-3-oxo-1-propenyl) cyclopropanecarboxylic acid

Product 1

HCID 543222844-Methoxymethylbezyl 2,2-dimethyl-3-(3-methoxy-3-oxo-1-propenyl)cyclopropanecarboxylateYield 94.8%

Reagents, catalysts & solvents

1
HCID 180AcetoneSolvent

Procedure

4.1 g of 2,2-dimethyl-3-(3-methoxy-3-oxo-1-propenyl) cyclopropanecarboxylic acid was dissolved in 50 ml of acetone, and 4.3 g of 4-methoxymethylbezylbromide was added to the solution. Next 2.4 g of triethylamine was added to the solution and underwent reaction at 60-80° C. for 3 hours while agitated, after which ether was added. After the ether solution was fully washed with diluted hydrochloric acid, sodium hydrogencarbonate aqueous solution and brine, it was dried with mirabilite. Ether was distilled under reduced pressure, and 6.3 g of 4-methoxymethylbezyl 2,2-dimethyl-3-(3-methoxy-3-oxo-1-propenyl)cyclopropanecarboxylate was obtained.

Workup

  1. washAfter the ether solution was fully washed with diluted hydrochloric acid, sodium hydrogencarbonate aqueous solution and brine, it
  2. dry with materialwas dried with mirabilite
  3. distillationEther was distilled under reduced pressure

Sources & evidence

ORD record
ord-72fb62b8cf3a46dd966bdcb72b3dd6d3
Source dataset
uspto-grants-2000_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06107339

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes