Sulfuric Acid → Benzenebutanol

HRID 1655497Notes

Reaction equation

HRID 1655497 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]1([CH2:13][CH2:14][CH2:15][C:16](O)=[O:17])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.S(=O)(=O)(O)O>O1CCCC1>[C:7]1([CH2:13][CH2:14][CH2:15][CH2:16][OH:17])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 47754-Phenylbutyric AcidHCID 21226445Aluminium lithium hydride

Product 1

HCID 76889Benzenebutanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of lithium aluminum hydride (67.2 g) in dry tetrahydrofuran (2.5 l), a solution of 4-phenylbutyric acid (225 g, 1.37 mmoles) in dry tetrahydrofuran was added dropwise at 15°-25° C. under nitrogen. The resultant mixture was stirred for 1 h at room temperature, then poured into ice-cold H2O (3 l) and sulfuric acid (200 g) and extracted thrice with ethyl acetate. The organic extract was dried over anhydrous N2SO4, evaporated, and then the residue was distilled under reduced pressure to give the title compound as a colorless oil; yield: 191 g; bp 113°-115° C./0.5 mmHg (Lit. bp 92°-93° C./0.3 mmHg; B. H. Baker, W. B. Martin, J. Org. Chem., 25, 1496 (1960)).

Workup

  1. extractionextracted thrice with ethyl acetate
  2. extractionThe organic extract
  3. customwas dried over anhydrous N2SO4
  4. customevaporated
  5. distillationthe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-2101282346794261b3c82d128a1bcb0f
Source dataset
uspto-grants-1993_10
Patent number
US05250669

Reaction notes

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