Hydrochloric Acid → HCID 118622746, compound

HRID 2202222Notes

Reaction equation

HRID 2202222 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([O:13]C)[CH:5]=[C:6]2[C:10]=1[C:9]([CH3:12])([CH3:11])[CH2:8][CH2:7]2.C(S)CCCCCCCCCCC.[Cl-].[Al+3].[Cl-].[Cl-].Cl>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([OH:13])[CH:5]=[C:6]2[C:10]=1[C:9]([CH3:11])([CH3:12])[CH2:8][CH2:7]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 81951-DodecanethiolHCID 6451240Aluminum(III) ChlorideHCID 68971478HCID 68971478, compound

Product 1

HCID 118622746HCID 118622746, compoundYield 94.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 7-fluoro-5-methoxy-1,1-dimethyl-2,3-dihydro-1H-indene (4.76 g, 24.51 mmol) and 1-dodecanethiol (17.71 mL, 73.52 mmol) in toluene (50 mL) was added aluminium chloride (9.80 g, 73.52 mmol) at 0° C., and the mixture was stirred at room temperature for 2 hr. To the reaction mixture was added 1N hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent; ethyl acetate/hexane) to give 7-fluoro-1,1-dimethyl-2,3-dihydro-1H-inden-5-ol (4.17 g, 23.14 mmol, 94%) as an off-white solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (solvent; ethyl acetate/hexane)

Sources & evidence

ORD record
ord-28d53884930c49f7a59635eadd6c4abb
Source dataset
uspto-grants-2016_06
Patent number
US09365520B2

Reaction notes

Loading…