Hydrochloric Acid → 3-(4-(tert-Butoxy)phenyl)propanoic acid

HRID 1862960Notes

Reaction equation

HRID 1862960 reaction equation
[N+](C1C=CC(C[O:9][C:10](=[O:24])[CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:15][CH:14]=2)=CC=1)([O-])=O.[OH-].[Na+].Cl>O1CCOCC1>[C:20]([O:19][C:16]1[CH:15]=[CH:14][C:13]([CH2:12][CH2:11][C:10]([OH:24])=[O:9])=[CH:18][CH:17]=1)([CH3:23])([CH3:21])[CH3:22]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 70606363HCID 70606363, compound

Product 1

HCID 195941973-(4-(tert-Butoxy)phenyl)propanoic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2.86 g (8 mmol) of 3-(4-tert.butoxyphenyl)-propionic acid 4-nitrobenzyl ester in 500 ml of dioxan are saponified while stirring with 8 ml of 2-N sodium hydroxide for 2 hours at 70° C. and for 12 hours at room temperature. After acidifying the solution with an equivalent amount of 1-N hydrochloric acid, the organic solvent is almost completely removed in vacuo and the residue partitioned between 40 ml of 0.5-N potassium hydrogen carbonate solution and diethyl ether. After cooling, the aqueous phase is cautiously acidified with 1-N hydrochloric acid and extracted several times with ethyl acetate. The combined organic phases are washed neutral with water, dried over sodium sulphate and evaporated in vacuo. A solution of the residue in heptane is filtered and evaporated to dryness in vacuo. There is obtained 3-(4-tert.butoxyphenyl)-propionic acid in the form of a crystalline residue of melting point 29°-31° C. The product is chromatographically pure in cyclohexane/chloroform/acetic acid (45:45:10). The yield amounts to 1.3 g (73% of theory).

Workup

  1. customthe organic solvent is almost completely removed in vacuo
  2. customthe residue partitioned between 40 ml of 0.5-N potassium hydrogen carbonate solution and diethyl ether
  3. temperatureAfter cooling
  4. extractionextracted several times with ethyl acetate
  5. washThe combined organic phases are washed neutral with water
  6. dry with materialdried over sodium sulphate
  7. customevaporated in vacuo
  8. filtrationA solution of the residue in heptane is filtered
  9. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-446e0763aa264f7fbc7442574cc0bfe2
Source dataset
uspto-grants-1979_09
Patent number
US04167508

Reaction notes

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