Ethanol → Ethyl (3,4,5-trifluoro-2-hydroxyphenyl)acetate

HRID 71218Notes

Reaction equation

[F:1][C:2]1[C:3]([OH:14])=[C:4]([CH2:10][C:11]([OH:13])=[O:12])[CH:5]=[C:6]([F:9])[C:7]=1[F:8].S(=O)(=O)(O)O.C(=O)([O-])O.[Na+].[CH2:25](O)[CH3:26]>>[F:1][C:2]1[C:3]([OH:14])=[C:4]([CH2:10][C:11]([O:13][CH2:25][CH3:26])=[O:12])[CH:5]=[C:6]([F:9])[C:7]=1[F:8]

Participants

Reactant 4

HCID 702Ethanol

HCID 1118Sulfuric Acid

HCID 516892Sodium Bicarbonate

HCID 84673812(3,4,5-Trifluoro-2-hydroxyphenyl)acetic acid

Product 1

HCID 86662985Ethyl (3,4,5-trifluoro-2-hydroxyphenyl)acetate

Conditions

Temperature: 80 °C

Procedure

A mixture of (3,4,5-trifluoro-2-hydroxyphenyl)acetic acid (6.0 g), sulfuric acid (0.016 mL) and ethanol (50 mL) was stirred at 80° C. overnight, neutralized with saturated aqueous sodium hydrogen carbonate solution, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (5.6 g).

Workup

concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record: ord-bd6a4b07710c43fd947d9e76e8c8b527
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822699B2

Reaction notes

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