Diethyl Ether → 3-(4-Fluorophenyl)propan-1-ol

HRID 719669

Reaction equation

HRID 719669 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10](O)=[O:11])=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].CCOCC>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][OH:11])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 1363023-(4-Fluorophenyl)propionic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 137472413-(4-Fluorophenyl)propan-1-olYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a THF (200 mL) solution containing 3-(4-fluorophenyl)propanoic acid (33.6 g, 0.2 mol) was added a 1.0 M solution of LiAlH4 in Et2O (200 mL, 0.2 mol) over a period of 0.5 h. The resulting mixture was allowed to stir at RT for 18 h. The reaction was slowly quenched with H2O and the aqueous layer extracted (1×) with Et2O. The combined organic extracts were dried over MgSO4 and concentrated in vacuo. The resulting oil was used in the next step without further purification. Isolated 31.4 g (0.2 mol, 100% yield).

Workup

  1. customThe reaction was slowly quenched with H2O
  2. extractionthe aqueous layer extracted (1×) with Et2O
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe resulting oil was used in the next step without further purification
  6. customIsolated 31.4 g (0.2 mol, 100% yield)

Sources & evidence

ORD record
ord-b35f9aebdb17443591baa6179bf6571a
Source dataset
uspto-grants-2006_11
Patent number
US07132443B2

Linked notes

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