Hydrochloric Acid → HCID 23501712, compound

HRID 1835607Notes

Reaction equation

HRID 1835607 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:10][CH:11]=[C:12]([CH2:14][CH2:15][O:16]S(C)(=O)=O)[CH:13]=2)=[CH:4][CH:3]=1.[OH-].[Na+].Cl>CO.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([O:21][CH2:22][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)=[CH:10][CH:11]=[C:12]([CH2:14][CH2:15][OH:16])[CH:13]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 23501804HCID 23501804, compound

Product 1

HCID 23501712HCID 23501712, compoundYield 69.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

5-(4-fluorophenyl)-4-benzyloxy-2-mesyloxyethylbenzene (2.5 g, 6.24 mmol) was dissolved in methanol (80 mL). To this was added sodium hydroxide (300 mg, 7.5 mmol) dissolved in water (20 mL). The solution was heated to reflux and heating maintained for 24 hours, when an additional equivalent of sodium hydroxide was added, and reflux maintained for an additional 16 hours. The mixture was cooled, acidified with 1N HCl, and extracted with ethyl acetate. The organic layers were dried over magnesium sulfate, filtered, and concentrated under reduced pressure to afford an orange solid which was triturated with hexane to yield 5-(4-fluorophenyl)-4-benzyloxy-2-hydroxyethylbenzene (1.4 g) as an off-white powder. NMR (DMSO-d6): 1.11, t, (3H); 2.50, q (2H); 3.34, s (3H); 5.02, s (2H); 6.60, d (1H); 6.98, s (1H); 7.16, t (2H); 7.35, m (5H); 7.50, dd (2H); 9.44, s (1H). Mass Spec (GCMS): 322 (M).

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux
  3. temperatureheating
  4. temperaturemaintained for 24 hours
  5. temperaturereflux
  6. temperaturemaintained for an additional 16 hours
  7. temperatureThe mixture was cooled
  8. extractionextracted with ethyl acetate
  9. dry with materialThe organic layers were dried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure
  12. customto afford an orange solid which
  13. customwas triturated with hexane

Sources & evidence

ORD record
ord-8ff68073664d456bae15bc0d88be06c3
Source dataset
uspto-grants-2004_08
Patent number
US06770259B2

Reaction notes

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