3-Cyclohexene-1-methanol → HCID 86703785, compound

HRID 1849907Notes

Reaction equation

HRID 1849907 reaction equation
[CH:1]1([CH2:7][OH:8])[CH2:6][CH2:5][CH:4]=[CH:3][CH2:2]1.[Cl:9][C:10]1[C:11](F)=[CH:12][C:13]([F:19])=[C:14]([CH:18]=1)[C:15]([OH:17])=[O:16].CC(C)([O-])C.[K+]>CS(C)=O.CCOC(C)=O>[Cl:9][C:10]1[C:11]([O:8][CH2:7][CH:1]2[CH2:6][CH2:5][CH:4]=[CH:3][CH2:2]2)=[CH:12][C:13]([F:19])=[C:14]([CH:18]=1)[C:15]([OH:17])=[O:16]

Participants

6

Reactant 3

HCID 155123-Cyclohexene-1-methanolHCID 148764175-Chloro-2,4-difluorobenzoic acidHCID 23665647Potassium tert-butoxide

Product 1

HCID 86703785HCID 86703785, compoundYield 97.7%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of cyclohex-3-en-1-ylmethanol (1.00 g) and 5-chloro-2,4-difluoro-benzoic acid (1.72 g) in DMSO (36 mL) at 14° C. (bath) was added potassium tert-butoxide (2.20 g) gradually. The mixture was stirred at that temp for 5 min then at rt for 30 min. Diluted with EtOAc, the contents were washed with 1:4 mixture of 1M HCl and 1M NaH2PO4 (3×) and brine, and dried (Na2SO4). After filtration and concentration, the product was obtained as white solid (2.48 g).

Workup

  1. waitat rt for 30 min
  2. washthe contents were washed with 1:4 mixture of 1M HCl and 1M NaH2PO4 (3×) and brine
  3. dry with materialdried (Na2SO4)
  4. filtrationAfter filtration and concentration

Sources & evidence

ORD record
ord-edfd5c54dee14f7b8afadf6fbc81ddd2
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

Loading…