Hydrochloric Acid → 1-Benzyloxy-4-phenyl-butan-2-ol

HRID 8188

Reaction equation

HRID 8188 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:12]1([CH2:18][CH2:19][Mg]Cl)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.Cl>O1CCCC1>[CH2:1]([O:8][CH2:9][CH:10]([OH:11])[CH2:19][CH2:18][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 108989(Phenylmethoxy)acetaldehydeHCID 178418865HCID 178418865, compound

Product 1

HCID 133473711-Benzyloxy-4-phenyl-butan-2-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

Benzyloxy-acetaldehyde (3.0 g, 20 mmol) is dissolved in tetrahydrofuran (200 mL), cooled to −78° C. This solution is treated with phenylethylmagnesium chloride (1.0 M in tetrahydrofuran, 24 mL, 24 mmol), and stirred for one hour. The mixture is allowed to warm to room temperature and stirred for 4 h. The mixture is treated with hydrochloric acid (1 M, 40 mL) and extracted with ethyl acetate. The combined organic extracts are washed with water and brine, dried over sodium sulfate, and filtered. The filtrate is concentrated in vacuo to provide the title compound, 4.0 g (80%), as a colorless liquid.

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred for 4 h
  3. extractionextracted with ethyl acetate
  4. washThe combined organic extracts are washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-da68cd3ff7414fb3bec916908e6cbd70
Source dataset
uspto-grants-2006_08
Patent number
US07087626B2

Linked notes

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