Hydrochloric Acid → Butanoic acid, 4-(3-chlorophenoxy)-

HRID 709399Notes

Reaction equation

HRID 709399 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1.[C:11]1(=[O:16])[O:15][CH2:14][CH2:13][CH2:12]1.Cl>>[Cl:3][C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][CH:9]=1)[O:10][CH2:14][CH2:13][CH2:12][C:11]([OH:16])=[O:15]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 7302Gamma-ButyrolactoneHCID 79333-ChlorophenolHCID 14798Sodium Hydroxide

Product 1

HCID 3014342Butanoic acid, 4-(3-chlorophenoxy)-

Conditions

Temperature
170 °C

Procedure

A dispersion was prepared by suspending 1 eq of NaOH (flakes) in 3-chlorophenol (1 eq). The obtained dispersion was heated to 170° C. up to complete solubilization of the base. 1.4 Eq. of γ-butyrolactone were then dropwise added maintaining the reaction mixture at 170° C. for 5 hours. The reaction mixture was then poured into ice and then acidified with HCl 6N. The reaction product was extracted with CHCl3, dehydrated over Na2SO4 and concentrated under vacuum. The residue was purified by flash chromatography (eluent oil ligroin/ethyl acetate 4:1 v/v) to obtain a yellow solid corresponding to 4-(3-chlorophenoxy)butyric acid. 27.96 mmoles of 4-(3-chlorophenoxy)butyric acid were added to 48 grams of polyphosphoric acid and the resulting mixture was maintained under stirring at 90° C. for 2 hours. At the end the reaction mixture was then poured on ice and extracted with CH2Cl2. The pooled organic phases were washed with a 10% Na2CO2 aqueous solution, dehydrated over Na2SO4, and concentrated under vacuum. The residue was purified by flash chromatography (oil ligroin/ethyl acetate 9/1 v/v). An orange oil corresponding to 8-chloro-1-oxo-2,3,4,5-tetrahydrobenzo-cycloheptan-5-one was obtained.

Workup

  1. customA dispersion was prepared
  2. temperaturemaintaining the reaction mixture at 170° C. for 5 hours
  3. additionThe reaction mixture was then poured into ice
  4. extractionThe reaction product was extracted with CHCl3
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by flash chromatography (eluent oil ligroin/ethyl acetate 4:1 v/v)

Sources & evidence

ORD record
ord-ce8210d077184bd0bf23a9551e75e9c5
Source dataset
uspto-grants-2015_11
Patent number
US09181196B2

Reaction notes

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