Water → HCID 53703941, compound

HRID 1730744Notes

Reaction equation

HRID 1730744 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([CH:14]([S:16]([CH2:18][C:19]([OH:21])=[O:20])=[O:17])[CH3:15])=[CH:10][CH:9]=1.[C:22]1(C)C=CC(S(O)(=O)=O)=CC=1.O>CO.COC(OC)(C)C>[CH3:22][O:20][C:19](=[O:21])[CH2:18][S:16]([CH:14]([C:11]1[CH:12]=[CH:13][C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])=[CH:9][CH:10]=1)[CH3:15])=[O:17]

Participants

6

Reactant 3

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 20348737HCID 20348737, compound

Product 1

HCID 53703941HCID 53703941, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 64952,2-DimethoxypropaneSolvent

Procedure

1.5 gm (50 millimols) of [1-(2'-fluoro-4-biphenylyl)-ethylsulfinyl]-acetic acid, m.p. 164°- 165° C, were dissolved in 3 ml of methanol and 1.2 ml of 2,2-dimethoxypropane, 100 mgm of p-toluenesulfonic acid were added to the solution, and the mixture was allowed to stand for 12 days at room temperature. Then, water was added and the ester was extracted with toluene. The organic extract was washed with water, dried and evaporated, and the residue was purified by chromatography on 75 gm of silicagel (grain size 0.05 - 0.2 mm) with cyclohexane/ethyl acetate = 1/4. The combined ester -containing fractions were evaporated, and the residue was recrystallized from 3 ml of isopropanol. Yield: 800 mgm (50% of theory); m.p. 77-79° C.

Workup

  1. extractionthe ester was extracted with toluene
  2. extractionThe organic extract
  3. washwas washed with water
  4. customdried
  5. customevaporated
  6. customthe residue was purified by chromatography on 75 gm of silicagel (grain size 0.05 - 0.2 mm) with cyclohexane/ethyl acetate = 1/4
  7. customThe combined ester -containing fractions were evaporated
  8. customthe residue was recrystallized from 3 ml of isopropanol

Sources & evidence

ORD record
ord-85373012613045329c130d2535d966b5
Source dataset
uspto-grants-1976_11
Patent number
US03993683

Reaction notes

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