Water → HCID 14423939, compound

HRID 621737Notes

Reaction equation

HRID 621737 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. temperaturewas heated
  2. washThe reaction mixture was washed with 1N NaOH (10 mL) while it
  3. temperaturewas warm and with water (100 mL)
  4. customConcentration of the organic layer gave off-white crystals of product
  5. customThis was purified by recrystallization from ethanol-hexane

Sources & evidence

ORD record
ord-2712efa124154cbbae99d5fbb66b7a0a
Source dataset
uspto-grants-1989_04
Patent number
US04824959

Reaction notes

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