Isopropanol → HCID 13207909, compound

HRID 1995516Notes

Reaction equation

HRID 1995516 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH:11]([CH3:13])[CH3:12])[C:9]#[N:10])=[CH:4][CH:3]=1.CC(O)C.[OH-].[Na+].Cl[CH:21]([F:23])[F:22]>CCOCC.O>[F:22][CH:21]([F:23])[O:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH:11]([CH3:13])[CH3:12])[C:9]#[N:10])=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 3776IsopropanolHCID 6372ChlorodifluoromethaneHCID 14798Sodium HydroxideHCID 13207908HCID 13207908, compound

Product 1

HCID 13207909HCID 13207909, compoundYield 81.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2-(4-hydroxyphenyl)-3-methylbutyronitrile (25.0 g; 0.1427 mol), 2-propanol (230 ml), and 25.8% aqueous sodium hydroxide (103 ml; 0.857 mol) is stirred in a pressure vessel and chlorodifluoromethane (36.4 g; 0.421 mol) is added over a period of 52 minutes with cooling to control the exotherm and to maintain the temperature of the reaction mixture below 52° C. The reaction mixture is then stirred for an additional 11/2 hours. Water (700 ml) and ether (300 ml) are then added to the reaction mixture and the two phase mixture is separated. The ether solution is washed twice with water (1000 ml+500 ml) and then with saturated brine (300 ml). It is then dried and evaporated under vacuum to yield 30.48 g (94.8%) of a clear, very slightly yellow liquid, shown to be 85.9% pure by gas-liquid chromatography. This corresponds to a yield of 81.4%.

Workup

  1. temperaturewith cooling
  2. temperatureto maintain the temperature of the reaction mixture below 52° C
  3. stirringThe reaction mixture is then stirred for an additional 11/2 hours
  4. customthe two phase mixture is separated
  5. washThe ether solution is washed twice with water (1000 ml+500 ml)
  6. customIt is then dried
  7. customevaporated under vacuum
  8. customto yield 30.48 g (94.8%) of a clear, very slightly yellow liquid

Sources & evidence

ORD record
ord-3209098568054342b3c7633a31bd35e3
Source dataset
uspto-grants-1983_09
Patent number
US04405529

Reaction notes

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