Isoprene → 3-Cyclohexene-1-acetic acid, 4-methyl-

HRID 651924

Reaktionsgleichung

Reaktionsgleichung von HRID 651924
C12C[CH2:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][CH2:3]O2.[CH:10]([CH:12]=[CH2:13])=[O:11].C=CC(=C)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C[Mg]Br.CCCCCCC([OH:50])CC>CCOCC>[CH3:8][C:5]1[CH2:6][CH2:7][CH:13]([CH2:12][C:10]([OH:50])=[O:11])[CH2:3][CH:4]=1

Komponenten

8

Edukt 6

HCID 6557IsopreneHCID 7847AcroleinHCID 11776TriphenylphosphineHCID 122163-NonanolHCID 201980142-Oxabicyclo[3.2.2]nonaneHCID 178418573HCID 178418573, Verbindung

Produkt 1

HCID 118049793-Cyclohexene-1-acetic acid, 4-methyl-

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

When m is 1, n is 2 and p is 2, the ring system is a 2-oxabicyclo[3.2.2]nonane, another subclass of this invention. For example, compound XVp ##STR30## in which R2, R5 and R6 are methyl can be prepared by treating a Diels-Alder adduct of acrolein and isoprene with Ph3P=C(CH3)OCH3, hydrolyzing the resulting enol ether, treating the resulting ketone derivative with methyl magnesium bromide, and subjecting the resulting alcohol to epoxidation-cyclization to yield a 2-oxabicyclo[3.2.2.]nonan-7-ol, which is treated with WCH2X in which X is a halogen atom to yield the desired ether, XVp. Alternatively, 4-methyl-3-cyclohexene-1-acetic acid, as obtained by the method of Kugatova-Shemyakina et al., Chemical Abstracts, 65:10504c (1966) is treated with methyl Grignard followed by epoxidation-cyclization of the resulting alcohol to yield a 2-oxabicyclo[3.2.2]nonan-7-ol.

Aufarbeitung

  1. customcan be prepared
  2. customto yield a 2-oxabicyclo[3.2.2

Quellen und Nachweise

ORD-Eintrag
ord-4158566907e747298c4ec84c5a13c6ef
Quelldatensatz
uspto-grants-1987_06
Patentnummer
US04670041

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