Ethanol → Ethyl 4-chloro-3-(trifluoromethyl)benzoate

HRID 423316Notes

Reaction equation

HRID 423316 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].S(=O)(=O)(O)O.[CH2:20](O)[CH3:21]>>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH2:20][CH3:21])=[O:7])=[CH:4][C:3]=1[C:11]([F:12])([F:13])[F:14]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 27738574-Chloro-3-(trifluoromethyl)benzoic acid

Product 1

HCID 46311320Ethyl 4-chloro-3-(trifluoromethyl)benzoate

Conditions

Temperature
100 °C

Procedure

4-Chloro-3-(trifluoromethyl)benzoic acid (1 g, 4.45 mmol) was dissolved in ethanol (3 ml) and concentrated sulfuric acid (0.15 ml) was added. The mixture was heated in the microwave at 100° C. for 5 minutes and then 120° C. for 15 minutes. The solvent was removed in vacuo and the residue partitioned between saturated aq. sodium bicarbonate (50 ml) and ethyl acetate (50 ml). The aqueous layer was extracted with further EtOAc (50 ml) and the organic phases were combined, dried with a phase separator and concentrated in vacuo to give the title compound (1.026 g) (DN108121-148A3) as a colourless oil. δH (methanol-d4, 400 MHz) 1.40 (3H, t), 4.41 (2H, q), 7.76 (1H, d), 8.21 (1H, dd), 8.33 (1H, d). MS (ES) no mass ion observed.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue partitioned between saturated aq. sodium bicarbonate (50 ml) and ethyl acetate (50 ml)
  3. extractionThe aqueous layer was extracted with further EtOAc (50 ml)
  4. customdried with a phase separator
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-248d688c36c04263bd7aa93ba0bb65da
Source dataset
uspto-grants-2012_01
Patent number
US08101775B2

Reaction notes

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