Sulfuric Acid → 1-[Bis(4-fluorophenyl)methoxy]-4-chlorobutane

HRID 1640333

Reaction equation

HRID 1640333 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][OH:6].S(=O)(=O)(O)O.[F:12][C:13]1[CH:27]=[CH:26][C:16]([CH:17](O)[C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)=[CH:15][CH:14]=1>C1(C)C=CC=CC=1>[F:12][C:13]1[CH:14]=[CH:15][C:16]([CH:17]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[O:6][CH2:5][CH2:4][CH2:3][CH2:2][Cl:1])=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 135694-Chloro-1-butanolHCID 1230494,4'-Difluorobenzhydryl alcohol

Product 1

HCID 107573721-[Bis(4-fluorophenyl)methoxy]-4-chlorobutaneYield 75%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4-chloro-1-butanol (6.51 g, 60 mmol), 1 mL of concentrated sulfuric acid and 4,4′-difluorobenzhydrol (2.2 g, 10 mmol) in 50 mL of toluene was heated at reflux for 12 h. The reaction mixture was cooled, washed successively with saturated sodium bicarbonate solution (50 mL) and water (50 mL). The organic layer was dried over MgSO4, filtered and the solvent was removed by rotary evaporation. The resultant brown oil was purified on a silica gel column. Elution with 2% ethyl acetate/hexane afforded 2.33 g (7.5 mmol, 75%) of the product as a colorless oil. 1H NMR (CDCl3): δ 1.71-1.80 (2H, m), 1.84-1.93 (2H, m), 3.43 (2H, t, J=6.0), 3.52 (2H, t, J=6.4), 5.30 (1H, s) 6.95-7.02 (4H, m), 7.24-7.29 (4H, m)

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 12 h
  3. temperatureThe reaction mixture was cooled
  4. washwashed successively with saturated sodium bicarbonate solution (50 mL) and water (50 mL)
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. customthe solvent was removed by rotary evaporation
  8. customThe resultant brown oil was purified on a silica gel column
  9. washElution with 2% ethyl acetate/hexane

Sources & evidence

ORD record
ord-bc4c2c5c6f984423a81075c58cf76e20
Source dataset
uspto-grants-2012_02
Patent number
US08114379B2

Linked notes

Loading…