Hydrochloric Acid → 2-(4-tert-butylphenoxy)propanoic acid

HRID 1704132Notes

Reaction equation

HRID 1704132 reaction equation
[H-].[Na+].[C:3]([C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)([CH3:6])([CH3:5])[CH3:4].Br[CH:15]([CH3:19])[C:16]([OH:18])=[O:17].Cl>CS(C)=O.O>[C:3]([C:7]1[CH:8]=[CH:9][C:10]([O:13][CH:15]([CH3:19])[C:16]([OH:18])=[O:17])=[CH:11][CH:12]=1)([CH3:6])([CH3:4])[CH3:5]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 73934-tert-ButylphenolHCID 117292-Bromopropionic acidHCID 24758Sodium hydride

Product 1

HCID 2468682-(4-tert-butylphenoxy)propanoic acid

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent3×HCID 962WaterSolvent

Procedure

To a chilled slurry of 9.3 g of sodium hydride-oil dispersion (57%) in 150 ml of dimethyl sulfoxide is added 15.0 g of p-tert-butylphenol in 50 ml of dimethyl sulfoxide and 18.9 g of 2-bromopropionic acid in 50 ml of dimethyl sulfoxide. The mixture is stirred at room temperature for 1/2 hr. and heated on a steam bath overnight. The mixture is diluted with 250 ml of water, acidified with 10 ml of conc. hydrochloric acid and extracted with ether. The ether extracts are dried (MgSO4) and the solvent removed under vacuum. Chromatography over silica gel with dichloromethane as eluent gives the product as white crystals, mp 86°-89° C.

Workup

  1. temperatureand heated on a steam bath overnight
  2. extractionextracted with ether
  3. dry with materialThe ether extracts are dried (MgSO4)
  4. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-32141a9d261442fb81b8057bbc273b68
Source dataset
uspto-grants-1978_11
Patent number
US04125732

Reaction notes

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