Sulfuric Acid → o-(Trifluoromethyl)benzaldehyde

HRID 1284911Notes

Reaction equation

HRID 1284911 reaction equation
[Mg].Br[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]([F:12])([F:11])[F:10].CN([CH:21]=[O:22])C1C=CC=CC=1.S(=O)(=O)(O)O>CCOCC>[F:10][C:9]([F:12])([F:11])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[CH:21]=[O:22]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 9806Benzene, 1-bromo-2-(trifluoromethyl)-HCID 66737N-MethylformanilideHCID 5462224Magnesium

Product 1

HCID 123067o-(Trifluoromethyl)benzaldehydeYield 68.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

2.8 Grams of metallic magnesium, 25 g of 2-bromo-α,α,α-trifluorotoluene and 120 ml of ether were reacted to prepare a Grignard ragent by a conventional method, then 15 g of N-methylformanilide were added dropwise thereto, and the reaction mixture was allowed to stand for 3 hours. Under an ice-cooled condition, a dilute sulfuric acid was added to the reaction mixture. The ethereal layer was separated and was washed with a saturated sodium chloride aqueous solution and with a saturated sodium hydrogencarbonate aqueous solution, then was dried with anhydrous sodium sulfate, and was concentrated. The residue was purified by distillation under reduced pressure to yield 13.2 g of 2-trifluoromethylbenzaldehyde. Boiling point: 62°-65° C. (at 17 mm-Hg).

Workup

  1. customto prepare a Grignard ragent by a conventional method
  2. temperatureUnder an ice-cooled condition
  3. customThe ethereal layer was separated
  4. washwas washed with a saturated sodium chloride aqueous solution and with a saturated sodium hydrogencarbonate aqueous solution
  5. dry with materialwas dried with anhydrous sodium sulfate
  6. concentrationwas concentrated
  7. distillationThe residue was purified by distillation under reduced pressure

Sources & evidence

ORD record
ord-9d544515277c4b0d813d4a207c38c1e9
Source dataset
uspto-grants-1986_01
Patent number
US04564619

Reaction notes

Loading…