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

HRID 236063Notes

Reaction equation

HRID 236063 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.C1(C)C=CC=CC=1>[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 1140TolueneSolvent

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 toluene (30 ml) is heated under stirring for 36 hours at 90° C. The mixture is then poured into a 1N hydrochloric acid solution (300 ml), the organic phase is separated and the aqueous phase is extracted again with toluene. The organic phases are combined, 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 product are identical to those given in Example 1.

Workup

  1. temperatureis heated
  2. customthe organic phase is separated
  3. extractionthe aqueous phase is extracted again with toluene

Sources & evidence

ORD record
ord-03403310bc644de583e02958f72cebac
Source dataset
uspto-grants-1987_02
Patent number
US04642376

Reaction notes

Loading…