trans-1-Methyl-4-(1-methylvinyl)cyclohex-2-en-1-ol → 3-(1,3-dithiolan-2-yl)-6a,7,10,10a-tetrahydro-6,6,9-trimethyl-6H-dibenzo[b,d]pyran-1-ol
Reaction equation
[S:1]1[CH2:5][CH2:4][S:3][CH:2]1[C:6]1[CH:7]=[C:8]([OH:13])[CH:9]=[C:10]([CH:12]=1)[OH:11].[C:14]1(O)([CH3:23])[CH2:19][CH2:18][CH:17]([C:20]([CH3:22])=[CH2:21])[CH:16]=[CH:15]1>>[S:1]1[CH2:5][CH2:4][S:3][CH:2]1[C:6]1[CH:7]=[C:8]([OH:13])[C:9]2[CH:18]3[CH2:19][C:14]([CH3:23])=[CH:15][CH2:16][CH:17]3[C:20]([CH3:22])([CH3:21])[O:11][C:10]=2[CH:12]=1Participants
Procedure
The compounds of formula I in which R is hydrogen can be prepared by reacting a 3,5 -dialkanoyloxybenzaldehyde (III) with 1,2-ethanedithiol to produce a 1,3-dialkanoyloxy-5-(1,3-dithiolan-2-yl)benzene (IV), hydrolyzing the 1,3-dialkanoyloxy ester to produce 5-(1,3-dithiolan-2-yl)resorcinol (V), reacting compound V with p-mentha-2,8-dien-1-ol to produce 3-(1,3-dithiolan-2-yl)-6a,7,10,10a-tetrahydro-6,6,9-trimethyl-6H-dibenzo[b,d]pyran-1-ol (VI) which is then subjected to oxidative cleavage conditions to produce a compound of formula I named 3-formyl-6a,7,10,10a-tetrahydro-6,6,9-trimethyl-6H-dibenzo[b,d]pyran-1-ol. This process can be represented as follows: ##STR9## wherein R5 represents a lower alkanoyl group, such as the acetyl, propionyl and butyryl groups.
Sources & evidence
- ORD record
- ord-ee442df3da1d48bbaebc676205045843
- Source dataset
- uspto-grants-1977_07
- Patent number
- US04036857
Reaction notes
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