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2-Chlorophenol → 4-(2-Chlorophenoxy)butanoic acid

HRID 14598
Notes
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Reaction equation

HRID 14598 reaction equation
[Na].[Cl:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[OH:9].[O:10]1[CH2:14][CH2:13][CH2:12][C:11]1=[O:15]>C(O)C>[Cl:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[O:9][CH2:14][CH2:13][CH2:12][C:11]([OH:15])=[O:10]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 72452-ChlorophenolHCID 7302Gamma-ButyrolactoneHCID 5360545Sodium

Product 1

HCID 30143434-(2-Chlorophenoxy)butanoic acidYield 80.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
150 °C

Procedure

To a solution of sodium (405 mg, 1.08 mmol) in ethanol (11.1 mL) was added 2-chlorophenol and the reaction mixture was stirred for 5 minutes before adding dihydro-furan-2-one (1.4 g, 16.1 mmol). The reaction mixture was stirred for 5 hours at 100° C. after which time the ethanol was slowly evaporated by continuous heating to 150° C. for another 12 hours. After such time the residue was dissolved in water (7 mL) and aqueous hydrochloric acid (1N) was added until precipitation occurred. The precipitate was isolated by filtration, washed with water and dried in vacuo to yield the title compound as yellow solid (2.79 g, 80.4%).

Workup

  1. customwas slowly evaporated
  2. dissolutionAfter such time the residue was dissolved in water (7 mL)
  3. additionaqueous hydrochloric acid (1N) was added until precipitation
  4. customThe precipitate was isolated by filtration
  5. washwashed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-cc003b4b1f0546ffbf7061ce23672dbe
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07732452B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes