Hydroxyphenylacetic acid → Benzyl 2-(4-hydroxyphenyl)acetate

HRID 1944168Notes

Reaction equation

HRID 1944168 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C=O)C>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 127Hydroxyphenylacetic acidHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

Product 1

HCID 11107524Benzyl 2-(4-hydroxyphenyl)acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
17.5 °C

Procedure

To 2-(4-hydroxyphenyl)acetic acid in DMF cooled to 0° C. was added K2CO3 and the solution was stirred for 30 min. Then, benzyl bromide was added and the solution stirred at 0° C. and was allowed to slowly warm to 15-20° C. After all the ice was melted the solution was poured into NH4Cl(sat) and extracted with EtOAc. The combined organics were dried (Na2SO4), filtered, and evaporated. Column chromatography (SiO2, 0-35% EtOAc/Hex) gave pure benzyl 2-(4-hydroxyphenyl)acetate (E301).

Workup

  1. stirringthe solution stirred at 0° C.
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organics were dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-dc6536b643ab431b8279947673fbfe18
Source dataset
uspto-grants-2013_03
Patent number
US08394826B2

Reaction notes

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