5-(1,1-Dimethylheptyl)resorcinol → 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 26167Notes

Reaction equation

HRID 26167 reaction equation
[CH3:1][C:2]([C:10]1[CH:11]=[C:12]([OH:17])[CH:13]=[C:14]([CH:16]=1)[OH:15])([CH3:9])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C[O:19][C:20]1[CH2:25][CH:24]=[C:23]([C:26](O)([CH3:28])[CH3:27])[CH2:22][CH:21]=1>ClCCl>[OH:17][C:12]1[C:13]2[C@H:22]3[CH2:21][C:20](=[O:19])[CH2:25][CH2:24][C@H:23]3[C:26]([CH3:28])([CH3:27])[O:15][C:14]=2[CH:16]=[C:10]([C:2]([CH3:1])([CH3:9])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[CH:11]=1

Participants

4

Reactant 2

HCID 918705-(1,1-Dimethylheptyl)resorcinolHCID 64542264-Methoxy-alpha,alpha-dimethylcyclohexa-1,4-diene-1-methanol

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The process according to claim 1, said process comprising reacting 5-(1,1-dimethylheptyl)resorcinol with 1-methoxy-4-(1-hydroxy-1-methylethyl)-1,4-cyclohexadiene in the presence of stannic chloride in dichloromethane at a temperature ranging from about -10° C. to about 40° C. to provide dl-cis-1-hydroxy-3-(1,1-dimethylheptyl)-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9H-dibenzo[b,d]pyran-9-one.

Workup

  1. customranging from about -10° C. to about 40° C.

Sources & evidence

ORD record
ord-2de0e76b38544812b57d65a96b8dfab1
Source dataset
uspto-grants-1979_04
Patent number
US04148809

Reaction notes

Loading…