Hydrochloric Acid → HCID 14534380, compound

HRID 2051447Notes

Reaction equation

HRID 2051447 reaction equation
[OH:1][CH:2]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:17])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)[CH3:3].[C:26](Cl)(=[O:28])[CH3:27].Cl>C1(C)C=CC=CC=1.N1C=CC=CC=1>[C:26]([O:1][CH:2]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:17])=[CH:12][CH:11]=2)=[CH:8][CH:9]=1)[CH3:3])(=[O:28])[CH3:27]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 14549129HCID 14549129, compound

Product 1

HCID 14534380HCID 14534380, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 1140TolueneSolvent

Procedure

29.9 g (0.09 mol) of III-15 was dissolved in a mixed solution of 150 ml of toluene and 50 ml of pyridine, followed by addition of 9.42 g (0.12 mol) of acetyl chloride at 15°-20° C. over a period of 2 hours. The mixture was maintained at the same temperature for 2 hours and then at 40°-45° C. for another 2 hours. The reaction mixture was cooled below 10° C. and added with 300 ml of 3N hydrochloric acid. After separating the liquid phase, the organic layer was washed with water, 5% sodium hydrogencarbonate and water successively in that order and concentrated under reduced pressure. The residue was purified by column chromatography to give 33.0 g (98% yield) of benzyl 4'-(1-acetoxyethyl)-4-biphenylcarboxylate (IV-15).

Workup

  1. temperatureThe mixture was maintained at the same temperature for 2 hours
  2. temperatureThe reaction mixture was cooled below 10° C.
  3. customAfter separating the liquid phase
  4. washthe organic layer was washed with water, 5% sodium hydrogencarbonate and water successively in that order
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-ebb6ee64e44b48329db423168fb18b5a
Source dataset
uspto-grants-1991_05
Patent number
US05019298

Reaction notes

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