Sulfuric Acid → HCID 18989445, compound

HRID 2395599Notes

Reaction equation

HRID 2395599 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([F:11])([F:10])[F:9].C([Li])CCC.[CH:17]([CH:19]=[CH2:20])=[O:18].OS(O)(=O)=O>C1COCC1.CCCCCC>[CH:19]([CH:17]([C:7]1[CH:6]=[CH:5][CH:4]=[C:3]([C:8]([F:9])([F:10])[F:11])[C:2]=1[F:1])[OH:18])=[CH2:20]

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 7847AcroleinHCID 9807Benzene, 1-fluoro-2-(trifluoromethyl)-HCID 178418339Butyllithium

Product 1

HCID 18989445HCID 18989445, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-70 °C

Procedure

A solution of 360 g (2.194 mol) of 1-fluoro-2-trifluoromethylbenzene in 3.4 l of anhydrous THF is cooled to -70° C. under a nitrogen atmosphere. 1.508 l (2.412 mol) of a 1.6M solution of n-butyllithium in hexane are added dropwise over 70 minutes while maintaining the temperature below -67° C. and then the mixture is stirred for 30 minutes at -70° C. 154 ml (2.305 mol) of acrolein are then added dropwise over 30 min while maintaining the temperature below -60° C. The mixture is then stirred for 30 min at -70° C. The mixture is allowed to return to room temperature and is poured onto a mixture of 3.8 kg of ice and 300 ml of concentrated H2SO4.

Workup

  1. temperaturewhile maintaining the temperature below -67° C.
  2. temperaturewhile maintaining the temperature below -60° C
  3. stirringThe mixture is then stirred for 30 min at -70° C
  4. customto return to room temperature

Sources & evidence

ORD record
ord-96d28091b44d4b42a48c56de162a4359
Source dataset
uspto-grants-1996_02
Patent number
US05489592

Reaction notes

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