Acetaldehyde → 1-(2-Chloro-4-methoxy-phenyl)-ethanol

HRID 2386800Notes

Reaction equation

HRID 2386800 reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][C:8]=1[Cl:15].[CH:16](=[O:18])[CH3:17].O>CCCCCC.C1COCC1>[Cl:15][C:8]1[CH:9]=[C:10]([O:13][CH3:14])[CH:11]=[CH:12][C:7]=1[CH:16]([OH:18])[CH3:17]

Participants

7

Reactant 4

HCID 177AcetaldehydeHCID 962WaterHCID 27568631-Bromo-2-chloro-4-methoxybenzeneHCID 178418339Butyllithium

Product 1

HCID 217555931-(2-Chloro-4-methoxy-phenyl)-ethanol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

A 1.6M solution of n-butyllithium in hexane (4 ml) was added to a solution of 4-bromo-3-chloroanisole (CAS Reg. No. 50638-46-5, 1.3 g) in THF (20 ml) at −78° C. The mixture was stirred for 30 min at −78° C. Acetaldehyde (0.7 ml) was added to the mixture. The mixture was allowed to warm to room temperature. Water (50 ml) was added and extracted with DCM. The combined organic layers were dried over Na2SO4 and concentrated to an oil to give the title compound (983 mg) as colorless oil. MS (m/e)=186 [M+].

Workup

  1. customat −78° C
  2. temperatureto warm to room temperature
  3. extractionextracted with DCM
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. concentrationconcentrated to an oil

Sources & evidence

ORD record
ord-17758e9202a64c38a19add3502df54d7
Source dataset
uspto-grants-2012_09
Patent number
US08268820B2

Reaction notes

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