Methallyl alcohol → 4-Chloro-2-(2-methyl-2-propen-1-yloxy)nitrobenzene

HRID 440651

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([OH:8])[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:18][C:19](=[CH2:22])[CH2:20]O>CC(=O)CC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([O:8][CH2:20][C:19]([CH3:22])=[CH2:18])[CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 30.0 g (0.17 mole) of 5-chloro-2-nitrophenol, 30.49 g (0.221 mole) of potassium carbonate, and 18.47 g (0.204 mole) of 2-methyl-2-propen-1-ol in 200 mL of 2-butanone was heated at 80° C. for approximately 16 hours. During this period the reaction changed color from orange to pale yellow. At the conclusion of this period the reaction mixture was filtered, and the filtrate was evaporated under reduced pressure, leaving 32.50 g of 4-chloro-2-(2-methyl-2-propen-1-yloxy)nitrobenzene as a solid residue, m.p. 47°-49° C.

Workup

waitDuring this period the reaction changed
filtrationAt the conclusion of this period the reaction mixture was filtered
customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record: ord-d371590700f54983b1d7d2d0dc81456b
Source dataset: uspto-grants-1996_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05521147

Linked notes

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