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Propylene Oxide → 1-(4-Chlorophenyl)propan-2-ol

HRID 912029
Notes
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Reaction equation

HRID 912029 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Mg]Br)=[CH:4][CH:3]=1.[CH2:10]1[O:13][CH:11]1[CH3:12]>CCOCC.C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:10][CH:11]([OH:13])[CH3:12])=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 6378Propylene OxideHCID 178478191HCID 178478191, compound

Product 1

HCID 124998511-(4-Chlorophenyl)propan-2-ol

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

General Procedure FF: To a THF (5 mL) solution of 1.0 M of 4-chlorophenylmagnesium bromide in Et2O (10.0 mL) was added a solution of propylene oxide (0.87 g, 15 mmol) in THF (5 mL) at −78° C. under nitrogen and stirred. The mixture was slowly warmed to rt. The mixture was quenched with sat. aq NH4Cl (10 mL) and then extracted with EtOAc (50 mL). The organic phase was washed with brine (10 mL) and dried over anhydrous sodium sulfate. The crude material was purified by silica gel chromatography using Hexane/EtOAc (80:20) as eluent to give the desired product as a colorless oil. 1H NMR (CDCl3, 400 MHz): δ=1.23-1.26 (m, 3H), 1.44 (d, J=3.8 Hz, 1H), 2.65-2.80 (m, 2H), 3.97-4.07 (m, 1H), 7.14-7.18 (m, 2H), 7.28-7.32 (m, 2H).

Workup

  1. customThe mixture was quenched with sat. aq NH4Cl (10 mL)
  2. extractionextracted with EtOAc (50 mL)
  3. washThe organic phase was washed with brine (10 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe crude material was purified by silica gel chromatography

Sources & evidence

ORD record
ord-c18e1662fb3342fab2f591260b13d0bd
Source dataset
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08022206B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes