Sulfuric Acid → 2,2,2-Trichloroethyl 3,5-dihydroxybenzoate

HRID 1745899Notes

Reaction equation

HRID 1745899 reaction equation
[Cl:1][C:2]([Cl:6])([Cl:5])[CH2:3][OH:4].[OH:7][C:8]1[CH:9]=[C:10]([CH:14]=[C:15]([OH:17])[CH:16]=1)[C:11](O)=[O:12].S(=O)(=O)(O)O>>[OH:7][C:8]1[CH:9]=[C:10]([CH:14]=[C:15]([OH:17])[CH:16]=1)[C:11]([O:4][CH2:3][C:2]([Cl:6])([Cl:5])[Cl:1])=[O:12]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 74243,5-Dihydroxybenzoic AcidHCID 8259Trichloroethanol

Product 1

HCID 154242232,2,2-Trichloroethyl 3,5-dihydroxybenzoateYield 61.4%

Conditions

Temperature
90 °C

Procedure

To freshly distilled 2,2,2-trichloroethanol (25 mL) was added 3,5-dihydroxybenzoic acid 4.50 g, 29.2 mmol) followed by concentrated sulfuric acid (1.0 mL), and mixture was stirred vigorously and heated at 90° C. for 48 h under nitrogen. The reaction mixture was cooled and evaporated to dryness under reduced pressure. The crude product was purified by flash chromatography eluting with CH2Cl2 gradually increasing to 1:10 diethyl ether/CH2Cl2, to give (2,2,2-trichloroethyl) 3,5-dihydroxybenzoate as a viscous oil (5.12 g, yield 61.4%).

Workup

  1. temperatureThe reaction mixture was cooled
  2. customevaporated to dryness under reduced pressure
  3. customThe crude product was purified by flash chromatography
  4. washeluting with CH2Cl2
  5. temperaturegradually increasing to 1:10 diethyl ether/CH2Cl2

Sources & evidence

ORD record
ord-3452fd216dcb49769a79e3b701a14341
Source dataset
uspto-grants-2006_03
Patent number
US07019453B2

Reaction notes

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