Hydrochloric Acid → HCID 20297261, compound

HRID 1389618Notes

Reaction equation

HRID 1389618 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH:11]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:16]1([SH:22])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[CH:23](Br)(Br)Br.[OH-:27].[K+].[Cl-].[Li+].Cl.[OH2:32]>O1CCOCC1>[C:16]1([S:22][CH:11]([C:10]2[CH:13]=[CH:14][CH:15]=[C:8]([O:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:9]=2)[C:23]([OH:32])=[O:27])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

9

Reactant 7

HCID 313Hydrochloric AcidHCID 962WaterHCID 5558BromoformHCID 7969ThiophenolHCID 14797Potassium HydroxideHCID 382843-PhenoxybenzaldehydeHCID 433294Lithium Chloride

Product 1

HCID 20297261HCID 20297261, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

1.10 g (5 mmols) of 3-phenoxybenzaldehyde, 0.83 g (7.5 mmols) of thiophenol, 1.3 g (5.1 mmols) of bromoform, 1.7 g (26 mmols) of potassium hydroxide (having a purity higher than 85%) and 0.424 g (10 mmols) of lithium chloride were added to a mixture of 5 ml of dioxane and 5 g of ice crump, and the resulting mixture was stirred vigorously for 5 hours at 0° C. and then 19 hours at room temperature. The reaction mixture was then diluted with water, rendered acidic with hydrochloric acid and extracted with methylene chloride. The extract was washed with water, dried over anhydrous magnesium sulfate and concentrated to remove the solvent to obtain a crude product of 2-phenylthio-2-(3-phenoxyphenyl)acetic acid in a quantative yield. The resulting crude product was purified by column chromatography eluting with hexane-diethyl ether (10:1 by volume) to obtain 1.54 g (92% yield) of the above product in a substantially pure form.

Workup

  1. custom19 hours
  2. customat room temperature
  3. extractionextracted with methylene chloride
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customto remove the solvent

Sources & evidence

ORD record
ord-6a70f40975d641d9b5acf12d9ed19e9c
Source dataset
uspto-grants-1981_01
Patent number
US04245108

Reaction notes

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