Hydroxyphenylacetic acid → HCID 14208885, compound

HRID 374839Notes

Reaction equation

HRID 374839 reaction equation
[K].[OH:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=[O:11])=[CH:5][CH:4]=1.[C:13]([O:19][CH2:20]Cl)(=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15]>CN(C)C=O>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][C:10]([O:12][CH2:20][O:19][C:13](=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15])=[O:11])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 127Hydroxyphenylacetic acidHCID 87885Chloromethyl pivalateHCID 5462222Potassium

Product 1

HCID 14208885HCID 14208885, compoundYield 70.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The potassium salt of 4-hydroxyphenylacetic acid (9.5 g. 0.05 mL) was suspended in dimethylformamide (25 mL). Chloromethyl pivalate (7.53 g, 0.05 mol) was added and the reaction mixture was stirred at room temperature for 24 hours. The reaction mixture was poured into ice water and extracted with ethyl acetate (100 mL) . The ethyl acetate layer was washed, first with aqueous 5% NaHCO3 (100 mL) and then twice with water, then was dried over anhydrous MgSO4, filtered and evaporated to yield pivalyloxymethyl 4-hydroxyphenylacetate, melting at 159°-161° C. (yield 70.2%).

Workup

  1. extractionextracted with ethyl acetate (100 mL)
  2. washThe ethyl acetate layer was washed, first with aqueous 5% NaHCO3 (100 mL)
  3. dry with materialtwice with water, then was dried over anhydrous MgSO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-78bf257090e44b9980341479439abae6
Source dataset
uspto-grants-1996_01
Patent number
US05482961

Reaction notes

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