Ammonium Chloride → HCID 54239004, compound

HRID 1419696Notes

Reaction equation

HRID 1419696 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([Cl:12])=[CH:9][CH:10]=[O:11])=[CH:4][CH:3]=1.[CH3:13][Mg]Br.[NH4+].[Cl-]>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([Cl:12])=[CH:9][CH:10]([OH:11])[CH3:13])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 264373-Chloro-3-(4-chlorophenyl)-2-propenalHCID 178418573HCID 178418573, compound

Product 1

HCID 54239004HCID 54239004, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a cooled (-78° C.) solution of 3-(4-chlorophenyl)-3-chloroacrolein (2.0 g, 10.4 mmol, obtained according to Hauptmann et al, Tetrahedron Lett. 1968, 1317) in dry THF (30 mL) was added dropwise a 3M solution of methylmagnesium bromide in THF (3.47 mL, 10.4 mmol). After the addition was complete, the reaction mixture was stirred at -78° C. for 0.5 h. Next, saturated aqueous NH4Cl solution was added and the mixture was concentrated. The resulting aqueous residue was extracted with CHCl3, dried, filtered, concentrated and purified by flash chromatography to give 4-(4-chlorophenyl)-4-chloro-3-buten-2-ol (1.54 g, 71%) as a colourless oil: 1H NMR (300 MHz, CDCl3) δ (TMS) 7.51 (dt, Jt =2.6, Jd =8.6, 2H, arom), 7.33 (dt, Jt =2.6, Jd =8.6, 2H, arom), 6.18 (d, J=7.5, 1H, =CH), 4.93 (quint, J=6.4, 1H, CHOH), 1.39 (d, J=6.4, 3H, CHCH3).

Workup

  1. additionAfter the addition
  2. concentrationthe mixture was concentrated
  3. extractionThe resulting aqueous residue was extracted with CHCl3
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by flash chromatography

Sources & evidence

ORD record
ord-d93598c3d2224a358a07564d4735705c
Source dataset
uspto-grants-1999_03
Patent number
US05888941

Reaction notes

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