Hydrochloric Acid → HCID 23359138, compound

HRID 232871Notes

Reaction equation

HRID 232871 reaction equation
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].C([C:10]1[CH:18]=[CH:17][C:13]([C:14]([OH:16])=[O:15])=[C:12]([CH2:19][O:20][C:21]2[CH:26]=CC(O)=[CH:23][CH:22]=2)[CH:11]=1)#N.O.Cl.[N:30]1C=CC=C[CH:31]=1>>[C:5]([O:4][C:1]1[CH:23]=[CH:22][C:21]([O:20][CH2:19][C:12]2([C:31]#[N:30])[CH:11]=[CH:10][CH:18]=[CH:17][CH:13]2[C:14]([OH:16])=[O:15])=[CH:26][CH:2]=1)(=[O:7])[CH3:6]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 23359208HCID 23359208, compound

Product 1

HCID 23359138HCID 23359138, compound

Procedure

Under ice cooling and stirring, 5.5 ml of acetic anhydride was added to 5.2 g of 4-cyano-2-(4-hydroxyphenoxy)methylbenzoic acid obtained in Reference example 23 dissolved in 15.6 ml of pyridine and the mixture was stirred at the same temperature for 1.5 hours. Water was added to the reaction mixture and the mixture was adjusted to about pH 2 with conc. hydrochloric acid and extracted with ethyl acetate. Then, the organic layer was washed with a saturated saline solution, 1N-hydrochloric acid and further a saturated saline solution and then dried over anhydrous sodium sulfate. The solvent was removed to obtain 5.36 g of a crude product of the title compound.

Workup

  1. customobtained in Reference example 23
  2. stirringthe mixture was stirred at the same temperature for 1.5 hours
  3. extractionextracted with ethyl acetate
  4. washThen, the organic layer was washed with a saturated saline solution, 1N-hydrochloric acid
  5. dry with materialfurther a saturated saline solution and then dried over anhydrous sodium sulfate
  6. customThe solvent was removed

Sources & evidence

ORD record
ord-49401f63030540308abde24b1e69a386
Source dataset
uspto-grants-1997_01
Patent number
US05591752

Reaction notes

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