Methane, dichloromethoxy- → 7-(4-Fluorophenyl)-7-(3-formyl-6-hydroxy-2,4,5-trimethylphenyl)heptanoic acid

HRID 373382Notes

Reaction equation

HRID 373382 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:17]2[C:22]([CH3:23])=[CH:21][C:20]([CH3:24])=[C:19]([CH3:25])[C:18]=2[OH:26])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:4][CH:3]=1.[CH3:27][O:28]C(Cl)Cl>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:17]2[C:18]([OH:26])=[C:19]([CH3:25])[C:20]([CH3:24])=[C:21]([CH:27]=[O:28])[C:22]=2[CH3:23])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 21004Methane, dichloromethoxy-HCID 110247607-(4-Fluorophenyl)-7-(2-hydroxy-3,4,6-trimethylphenyl)heptanoic acid

Product 1

HCID 151251387-(4-Fluorophenyl)-7-(3-formyl-6-hydroxy-2,4,5-trimethylphenyl)heptanoic acid

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 7-(4-fluorophenyl)-7-(2-hydroxy-3,4,6-trimethylphenyl)heptanoic acid (7.5 g) and dichloromethyl methyl ether (5.7 ml) in dichloromethane (80 ml) was added a solution of titanium tetrachloride (6.9 ml) in dichloromethane (40 ml) over about 2 hours with ice-sodium chloride cooling. The reaction mixture was added to ice-water and the mixture was stirred for 30 minutes. The mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated saline and dried with anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting crystals were recrystallized from acetonitrile to obtain 7-(4-fluorophenyl)-7-(3-formyl-6-hydroxy-2,4,5-trimethylphenyl)heptanoic acid (7.8 g) (Compound 27). The physical properties and spectrum data thereof are shown in Tables 3 and 4.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated saline
  3. dry with materialdried with anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe resulting crystals were recrystallized from acetonitrile

Sources & evidence

ORD record
ord-044135c391d64e87942f863b2cf164c1
Source dataset
uspto-grants-1992_11
Patent number
US05162571

Reaction notes

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