Flocoumafen → 104563-60-2

HRID 2231721Notes

Reaction equation

HRID 2231721 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][C:4](=[O:12])[C:3]=1[CH:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][CH:15]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH2:30][C:31]3[CH:36]=[CH:35][C:34]([C:37]([F:40])([F:39])[F:38])=[CH:33][CH:32]=3)=[CH:25][CH:24]=2)[CH2:14]1>C(O)C>[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][C:4](=[O:12])[C:3]=1[C@H:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][C@H:15]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH2:30][C:31]3[CH:32]=[CH:33][C:34]([C:37]([F:40])([F:38])[F:39])=[CH:35][CH:36]=3)=[CH:25][CH:24]=2)[CH2:14]1

Participants

3

Reactant 1

HCID 54698175Flocoumafen

Product 1

HCID 76960466104563-60-2

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

An approximately 1:1 mixture of the cis and trans isomers of 1-(4-hydroxycoumarin-3-yl)-3-[4-(4-trifluoromethylbenzyloxy)phenyl]-1,2,3,4-tetrahydronaphthalene in the form of a viscous oil (13.0 g) was dissolved in ethanol (250 cm3) at the ambient temperature and the solution kept in an open flask at the ambient temperature for 3 days during which time some of the ethanol evaporated and some precipitation of a solid material occurred. This was collected by filtration and dried to give trans-1-(4-hydroxycoumarin-3-yl)-3-[4-(4trifluoromethylbenzyloxy)phenyl]-1,2,3,4-tetrahydronaphthalene (containing 7% by weight of the cis-isomer, 1.5 g), melting point 153°-155° C. The filtrate was concentrated by removal of the ethanol by evporation under reduced pressure. The residual oil was then dissolved in boiling ethanol (100 cm3) and the solution allowed to cool to 35° to 40° C. and maintained at this temperature whilst a precipitate formed rapidly. This was collected by filtration and dried to give cis-1-(4-hydroxycoumarin-3-yl)-3-[4-trifluoromethylbenzyloxy)phenyl]-1,2,3,4-tetrahydronaphthalene (containing 5% by weight of the transisomer, 5.5 g) melting point 183°-184.5° C.

Workup

  1. customsome of the ethanol evaporated
  2. customsome precipitation of a solid material
  3. filtrationThis was collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-0a7ff39db83445a8a5f72e53993631e9
Source dataset
uspto-grants-1988_11
Patent number
US04783481

Reaction notes

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