Tetrahydrofuran → Anisole

HRID 930797Notes

Reaction equation

HRID 930797 reaction equation
CO.O.[CH3:4][C:5]([CH3:7])=[O:6].C[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[C:15](OCC)(=[O:17])[CH3:16].[O:21]1CCC[CH2:22]1>CC(C)=O.C(OC)(C)(C)C.O1CCOCC1.C(#N)C.C(O)C.CO.[N+](C)([O-])=O.C(C(C)=O)C.C(C(C)=O)C(C)C>[C:15]([O:6][CH:5]([CH3:7])[CH3:4])(=[O:17])[CH3:16].[C:14]1([O:21][CH3:22])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

15

Reactant 4

HCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 21879760Acetone heptaneHCID 22242641Methanol--water (1/1)

Product 2

HCID 7519AnisoleHCID 7915Isopropyl Acetate

Reagents, catalysts & solvents 9

HCID 180AcetoneSolventHCID 702EthanolSolventHCID 887MethanolSolventHCID 6342AcetonitrileSolventHCID 6375NitromethaneSolventHCID 6569Methyl Ethyl KetoneSolventHCID 7909Methyl Isobutyl KetoneSolventHCID 15413tert-Butyl methyl etherSolventHCID 312751,4-DioxaneSolvent

Procedure

In some embodiments, Form A was obtained from ethyl acetate, isopropyl acetate, tetrahydrofuran, methyl isobutyl ketone (MIBK), methyl ethyl ketone (MEK), nitromethane, methanol, ethanol, acetonitrile, dioxane, methyl tert-butyl ether (MTBE), anisole, acetone, heptanes, a methanol/water mixture or an acetone/heptane mixture. In some embodiments, Form A was obtained from ethyl acetate, isopropyl acetate, tetrahydrofuran, methyl isobutyl ketone (MIBK), methyl ethyl ketone (MEK), nitromethane, methanol, ethanol, acetonitrile, dioxane, methyl tert-butyl ether (MTBE), anisole, acetone, heptanes, or an acetone/heptane mixture.

Sources & evidence

ORD record
ord-686cd6958816481c94a3ba373e43cc8f
Source dataset
uspto-grants-2016_03
Patent number
US09296753B2

Reaction notes

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