Hydrochloric Acid → 2-(4-Hydroxyphenyl)propionic acid

HRID 236062Notes

Reaction equation

HRID 236062 reaction equation
Br[CH:2]([C:4]1([C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=2)OCC(C)(C)CO1)C.[C:19](=O)([O-:21])[O-:20].[K+].[K+].Cl>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O>[OH:18][C:15]1[CH:14]=[CH:13][C:12]([CH:4]([CH3:2])[C:19]([OH:21])=[O:20])=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 202181682-(1'-Bromoethyl)-5,5-dimethyl-2-(4'-hydroxyphenyl)-1,3-dioxane

Product 1

HCID 1025262-(4-Hydroxyphenyl)propionic acidYield 30%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2-(1'-bromoethyl)-5,5-dimethyl-2-(4'-hydroxyphenyl)-1,3-dioxane (3.15 g; 0.01 mole), potassium carbonate (6.8 g; 0.05 mole), tetrabutylammonium bromide (0.06 g; 0.0002 mole) in dimethylformamide (30 ml) is heated while being stirred for 36 hours at 90° C. The mixture is then cooled to room temperature, poured into a 1N solution of HCl (300 ml), and extracted with toluene. The organic phase is evaporated and the residue is hydrolyzed as in Example 1c, to obtain 2-(4'-hydroxyphenyl)-propionic acid (0.49 g; 0.003 mole; yield of 30%). The characteristics of the acid are identical to those of Example 1.

Workup

  1. temperatureis heated
  2. temperatureThe mixture is then cooled to room temperature
  3. extractionextracted with toluene
  4. customThe organic phase is evaporated

Sources & evidence

ORD record
ord-b7b6c215e14f45a387a531de606851f2
Source dataset
uspto-grants-1987_02
Patent number
US04642376

Reaction notes

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