Sodium Hydroxide → 2-Propen-1-ol, 3-(3,4-dichlorophenyl)-

HRID 481431

Reaction equation

HRID 481431 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11](OC)=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8].CC(C[Al]CC(C)C)C.[OH-].[Na+].[O-]S([O-])(=O)=O.[Mg+2]>C1COCC1.CCOCC.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH2:11][OH:12])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

8

Reactant 4

HCID 14798Sodium Hydroxide2×HCID 24083Sulfuric acid magnesium salt (1:1)HCID 16682954DibahHCID 54151376Methyl 3-(3,4-dichlorophenyl)prop-2-enoate

Product 1

HCID 537091912-Propen-1-ol, 3-(3,4-dichlorophenyl)-Yield 100%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Treat a solution of the product of Step 1 (15 g, 65 mmol) in dry THF (250 mL), kept cool in a large ambient temperature water bath, with Dibal-H (140 mL, 140 mmol, 2.15 eq) over 30 min. Stir the resulting solution for 30 min at 23° C., pour into Et2O (500 mL), treat with water (5 mL), 15% NaOH (5 mL) and water (15 mL). Stir for 5 min, dilute the mixture with Et2O (200 mL) and treat with 15% NaOH (15 mL). Add MgSO4 to cause a colorless precipitate. Remove the aluminum salts by filtration through a course glass frit. Wash the solids with Et2O (1 L) and concentrate the filtrate in vacuo to give 13.2 g (65 mmol, 99%) of 3-(3,4-dichlorophenyl)-2-propene-1-ol as an off-white solid.

Workup

  1. stirringStir for 5 min
  2. customRemove the aluminum salts
  3. filtrationby filtration through a course glass frit
  4. washWash the solids with Et2O (1 L)
  5. concentrationconcentrate the filtrate in vacuo

Sources & evidence

ORD record
ord-716fd709c60340bfaf11c3a86ab0967a
Source dataset
uspto-grants-1998_08
Patent number
US05789422

Linked notes

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