Water → HCID 14423939, compound

HRID 330668Notes

Reaction equation

HRID 330668 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)(O)[CH:9]([C:11]2[N:15]([CH3:16])[N:14]=[N:13][N:12]=2)[CH3:10])=[CH:4][CH:3]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C(C)=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:18]2[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=2)=[C:9]([C:11]2[N:15]([CH3:16])[N:14]=[N:13][N:12]=2)[CH3:10])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 521998p-Toluenesulfonic acid monohydrateHCID 14423937HCID 14423937, compound

Product 1

HCID 14423939HCID 14423939, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A slurry of 1,1-bis(4-fluorophenyl)-2-(1-methyl-1H-tetrazol-5-yl)propanol (8.25 g, 0.025 mole) [prepared in Step B] and 100 mg of p-toluene sulfonic acid monohydrate in xylene (60 mL) was heated to reflux with a Dean & Stark water collecting apparatus for a period of 12 hours. The reaction mixture was washed with 1N NaOH (10 mL) while it was warm and with water (100 mL). Concentration of the organic layer gave off-white crystals of product. This was purified by recrystallization from ethanol-hexane to give 7.1 g (91%) of the title compound as white crystals; m.p.=146°-147° C.

Workup

  1. washThe reaction mixture was washed with 1N NaOH (10 mL) while it
  2. temperaturewas warm and with water (100 mL)
  3. customConcentration of the organic layer gave off-white crystals of product
  4. customThis was purified by recrystallization from ethanol-hexane

Sources & evidence

ORD record
ord-73bfe9b31d5142a5ae35d2c5e70eeeb2
Source dataset
uspto-grants-1990_01
Patent number
US04897490

Reaction notes

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