Hydroxyphenylacetic acid → Tert-butyl 2-(4-hydroxyphenyl)acetate

HRID 1927735Notes

Reaction equation

HRID 1927735 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>C1COCC1>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][C:5]([CH3:8])([CH3:6])[CH3:4])=[O:10])=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 127Hydroxyphenylacetic acid

Product 1

HCID 15932404Tert-butyl 2-(4-hydroxyphenyl)acetateYield 116.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(4-hydroxyphenyl)acetic acid (1.0 g, 6.57 mmol) was diluted with THF (4 mL) followed by the addition of Reactant 2 (2.63 g, 13.1 mmol). The reaction was stirred for hours 12 hours. The reaction was filtered and loaded directly onto a biotage 40M cartridge eluting with hexanes:ethyl acetate (3:1) to yield tert-butyl 2-(4-hydroxyphenyl)acetate (800 mg, 58.4% yield) as a clear oil that later solidified to a white solid.

Workup

  1. filtrationThe reaction was filtered
  2. washeluting with hexanes:ethyl acetate (3:1)

Sources & evidence

ORD record
ord-1e5ac5ad97a2409989fd56006e290542
Source dataset
uspto-grants-2012_05
Patent number
US08183289B2

Reaction notes

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