Hydrochloric Acid → 4-((3-(Azido(phenyl)methyl)phenoxy)methyl)benzoic acid

HRID 332676Notes

Reaction equation

HRID 332676 reaction equation
[N:1]([CH:4]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:5]1[CH:6]=[C:7]([CH:20]=[CH:21][CH:22]=1)[O:8][CH2:9][C:10]1[CH:19]=[CH:18][C:13]([C:14]([O:16]C)=[O:15])=[CH:12][CH:11]=1)=[N+:2]=[N-:3].[OH-].[Na+].O1CCCC1.Cl>CO>[N:1]([CH:4]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:5]1[CH:6]=[C:7]([CH:20]=[CH:21][CH:22]=1)[O:8][CH2:9][C:10]1[CH:19]=[CH:18][C:13]([C:14]([OH:16])=[O:15])=[CH:12][CH:11]=1)=[N+:2]=[N-:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 71093296Methyl 4-((3-(azido(phenyl)methyl)phenoxy)methyl)benzoate

Product 1

HCID 710930924-((3-(Azido(phenyl)methyl)phenoxy)methyl)benzoic acidYield 99.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred suspension of methyl 4-((3-(azido(phenyl)methyl)phenoxy)-methyl)benzoate (1 g, 2.79 mmol) in methanol (25 mL), was added 2M sodium hydroxide (25 mL). The reaction was allowed to stir at room temperature for 3 days. Tetrahydrofuran (10 mL) was added to the reaction mixture, and the mixture was stirred at 50° C. for 4 hours followed by 16 hours at room temperature. The reaction mixture was acidified with 10% hydrochloric acid, extracted with dichloromethane, dried (sodium sulphate), filtered, and concentrated under reduced pressure to give the title compound (1 g, quantitative).

Workup

  1. stirringthe mixture was stirred at 50° C. for 4 hours
  2. waitfollowed by 16 hours at room temperature
  3. extractionextracted with dichloromethane
  4. dry with materialdried (sodium sulphate)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d4ac373e0aa147d0a9550cfc2e14dca4
Source dataset
uspto-grants-2014_11
Patent number
US08877774B2

Reaction notes

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