Hydrochloric Acid → HCID 89451902, compound

HRID 1497530Notes

Reaction equation

HRID 1497530 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15]C)=[O:14].[OH-].[Na+].Cl>CO>[Cl:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 90282080HCID 90282080, compound

Product 1

HCID 89451902HCID 89451902, compoundYield 103.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 5-(2-chloro-4-hydroxyphenyl)pentanoate (2.28 g) in methanol (20.0 mL) was added a 1 M aqueous sodium hydroxide solution (28.2 mL), followed by stirring at room temperature for 1 hour. To a reaction solution was added 1 M hydrochloric acid (28.2 mL), followed by extraction with chloroform. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain 5-(2-chloro-4-hydroxyphenyl)pentanoic acid (2.22 g) as a mixture.

Workup

  1. extractionfollowed by extraction with chloroform
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-df71438ecdb4456fbd22e651d9c7e328
Source dataset
uspto-grants-2015_12
Patent number
US09199927B2

Reaction notes

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