Benzaldehyde → HCID 14291989, compound

HRID 359207Notes

Reaction equation

HRID 359207 reaction equation
[C:1]1([S:7]([CH:10]([F:12])[F:11])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].[CH:15](=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].ClCCl>[F:11][C:10]([F:12])([S:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)(=[O:9])=[O:8])[CH:15]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[OH:22]

Participants

6

Reactant 3

HCID 240BenzaldehydeHCID 14798Sodium HydroxideHCID 11816356((Difluoromethyl)sulfonyl)benzene

Product 1

HCID 14291989HCID 14291989, compoundYield 90.3%

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 100 mg (0.52 mmol) of difluoromethyl phenyl sulfone, 1.0 mL of dichloromethane, 1.0 mL of 50% aqueous sodium hydroxide and 20 mg (0.050 mmol) of Aliquat 336 was stirred vigorously for 10 minutes and treated with a solution of 0.16 mL (1.6 mmol) of benzaldehyde in 0.5 mL of dichloromethane. Vigorous stirring was continued for four hours and the resulting mixture was poured into 20 mL of lN HCL. Extraction of the aqueous mixture with three 10 mL portions of dichloromethane followed by combination, drying (MgSO4), and concentration in vacuo of the organic layers gave a residue which was purified by preparative TLC (two 2 mm silica gel plates eluted with dichloromethane), affording 140 mg (90% yield) of 2,2-difluoro-1-phenyl-2-phenylsulfonylethanol as a solid. Crystallization from toluene provided an analytical sample: mp 77°-79° C.; IR (neat) 3503, 3064, 2922, 1447, 1335, 1312, 1197, 1154, 1113, 1089, 996, 738, 715, 698, 685, 585, 558, cm-1 : lHNMR (CDCl3) δ3.54 (broad s, IH), 5.54 (dd, IH, JHF =21, 3 Hz), 7.20-8.10 (m, 10H); 19F NMR (CDCl3, relative to CFCl3)-106.4 ppm (dd, IF, JFF =238 Hz, JHF =3Hz), -121.6 ppm (dd, lF, JFF =238 Hz, JHF =21 Hz); mass spectrum (70 eV) m/e (relative intensity) 298 (8, M+), 156(18), 109(31), 107(100), 79(30), 78(18), 77(56), 51(20). Anal. Calcd. for C14H12F2O3S:C, 56.37; H, 4.06. Found: C, 56.58; H, 4.08.

Workup

  1. stirringVigorous stirring
  2. waitwas continued for four hours
  3. additionthe resulting mixture was poured into 20 mL of lN HCL
  4. extractionExtraction of the aqueous mixture with three 10 mL portions of dichloromethane
  5. customdrying
  6. concentration(MgSO4), and concentration in vacuo of the organic layers
  7. customgave a residue which
  8. customwas purified by preparative TLC (two 2 mm silica gel plates eluted with dichloromethane)

Sources & evidence

ORD record
ord-f56bacec31994b2999ca60befeaae3e5
Source dataset
uspto-grants-1991_03
Patent number
US04999429

Reaction notes

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