p-Toluenesulfonic acid → cis-1-hydroxy-3-(1,1-dimethylheptyl)-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9H-dibenzo[b,d]-pyran-9-one

HRID 867130Notes

Reaction equation

HRID 867130 reaction equation
[CH3:1][C:2]([C:10]1[CH:15]=[C:14]([OH:16])[C:13]([CH:17]2[CH:22]3[CH2:23][CH:20]([C:21]3([CH3:25])[CH3:24])[C:19](=[O:26])[CH2:18]2)=[C:12]([OH:27])[CH:11]=1)([CH3:9])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C1(C)C=CC(S(O)(=O)=O)=CC=1>>[OH:16][C:14]1[C:13]2[C@H:17]3[CH2:18][C:19](=[O:26])[CH2:20][CH2:23][C@H:22]3[C:21]([CH3:25])([CH3:24])[O:27][C:12]=2[CH:11]=[C:10]([C:2]([CH3:1])([CH3:9])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[CH:15]=1

Participants

3

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 11501631HCID 11501631, compound

Product 1

HCID 86735145cis-1-hydroxy-3-(1,1-dimethylheptyl)-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9H-dibenzo[b,d]-pyran-9-one

Procedure

The process according to claim 5 wherein optically active 4-[4-(1,1-dimethylheptyl)-2,6-dihydroxyphenyl]-6,6-dimethyl-2-norpinanone is reacted with para-toluenesulfonic acid to provide optically active cis-1-hydroxy-3-(1,1-dimethylheptyl)-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9H-dibenzo[b,d]pyran-9-one.

Sources & evidence

ORD record
ord-abdcda36e42c45a48eb5a2c2b59c9a60
Source dataset
uspto-grants-1978_07
Patent number
US04102902

Reaction notes

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