Heptane → 2-Hydroxy-2'-methoxybenzophenone

HRID 434204Notes

Reaction equation

HRID 434204 reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][CH:16]=[CH:15][C:4]=1[C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13]C)=[O:6].B(Cl)(Cl)Cl.CCCCCCC.C(=O)(O)[O-].[Na+]>ClCCl>[OH:13][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[C:5]([C:4]1[CH:15]=[CH:16][CH:17]=[CH:18][C:3]=1[O:2][CH3:1])=[O:6]

Participants

6

Reactant 4

HCID 8900HeptaneHCID 25135Boron TrichlorideHCID 516892Sodium BicarbonateHCID 5847282,2'-Dimethoxybenzophenone

Product 1

HCID 100596522-Hydroxy-2'-methoxybenzophenone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

This procedure is based on that reported in Tetrahedron Lett., 1966, 4153. To a solution of 2,2′-dimethoxybenzophenone (11) (6.7 g, 0.0277 mol) in anhydrous dichloromethane (95 mL) cooled to −65° C. under nitrogen was added 52 mL of a 1.0 M solution of boron trichloride in heptane (0.052 mol). The mixture was allowed to warm to room temperature and stirred for 75 minutes. The reaction mixture was slowly poured into a cold (0° C.) solution of saturated aqueous sodium bicarbonate, which was then extracted with dichloromethane. The organic extracts were washed with water and saturated with NaCl, followed by drying over anhydrous sodium sulfate. Analytically pure product was obtained after removal of the solvent in quantitative yield.

Workup

  1. extractionwas then extracted with dichloromethane
  2. washThe organic extracts were washed with water and saturated with NaCl
  3. dry with materialby drying over anhydrous sodium sulfate
  4. customAnalytically pure product was obtained
  5. customafter removal of the solvent in quantitative yield

Sources & evidence

ORD record
ord-34d65f855d0f4d31aa332e2a1e25a953
Source dataset
uspto-grants-2003_12
Patent number
US06670512B2

Reaction notes

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