Carvone, (+-)- → 4a-Carboethoxy-7-hydroxy-4,4a,5,6-tetrahydro-2(3H)-naphthalenone

Reaction equation

[CH3:1][CH2:2][O:3][C:4]([CH:6]1[C:12]([CH3:13])=[CH:11][C:9](=[O:10])[CH2:8][CH2:7]1)=[O:5].CC1[C:20](=[O:21])[CH2:19][CH:18](C(C)=C)CC=1.ClCCC(OCC)=O.C(C(CC)=O)=C>>[C:4]([C:6]12[CH2:18][CH2:19][C:20]([OH:21])=[CH:13][C:12]1=[CH:11][C:9](=[O:10])[CH2:8][CH2:7]2)([O:3][CH2:2][CH3:1])=[O:5]

Participants

Reactant 4

HCID 7439Carvone, (+-)-

HCID 153941-Penten-3-one

HCID 69341Ethyl 3-chloropropionate

HCID 790204-Carbethoxy-3-methyl-2-cyclohexen-1-one

Product 1

HCID 139503394a-Carboethoxy-7-hydroxy-4,4a,5,6-tetrahydro-2(3H)-naphthalenone

Procedure

This material is prepared according to the procedure for Preparation 6 wherein Hagemann's ester (ethyl 2-methyl-4-oxocyclohex-2-enyl-1-carboxylate) is substituted for carvone and ethyl 3-chloropropionate is substituted for ethyl vinyl ketone.