Water → (1-Phenylcyclopentyl)methanol

HRID 1729065Notes

Reaction equation

HRID 1729065 reaction equation
C[O:2][C:3]([C:5]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:9][CH2:8][CH2:7][CH2:6]1)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[C:10]1([C:5]2([CH2:3][OH:2])[CH2:9][CH2:8][CH2:7][CH2:6]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 11790325Methyl 1-phenylcyclopentane-1-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 123544(1-Phenylcyclopentyl)methanolYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of the product of Step A (3.00 g, 14.71 mmol) in 10 mL THF was added dropwise to a suspension of LiAlH4 (1.25 g, 33.09 mmol) in 25 mL dry THF. The reaction mixture was stirred at reflux for three hours. The excess LiAlH4 was destroyed following the method described in Reagents for Organic Synthesis, Vol 1 [1967] p. 584 (J. Wiley & Son), by quenching the cooled reaction mixture with the addition of 1.25 mL water, followed by the addition of 1.25 mL 154 sodium hydroxide (w/v), followed by the addition of 3.75 mL water. The resulting aluminum salts were separated by filtration and washed with water (5×1 mL). The product was extracted with ether (3×25 mL) and dried (Na2SO4). Evaporation of the solvent gave 2.07 g (88%) of 1-phenylcyclopentanemethanol as a white solid, mp 41°-44° C.(the literature value of mp, J. Org. Chem. 27:3434 (1962), is 43°-44° C.).

Workup

  1. temperatureat reflux for three hours
  2. customThe excess LiAlH4 was destroyed
  3. customdescribed in Reagents for Organic Synthesis, Vol 1 [1967] p
  4. custom584 (J. Wiley & Son), by quenching
  5. customthe cooled reaction mixture
  6. customThe resulting aluminum salts were separated by filtration
  7. washwashed with water (5×1 mL)
  8. extractionThe product was extracted with ether (3×25 mL)
  9. dry with materialdried (Na2SO4)
  10. customEvaporation of the solvent

Sources & evidence

ORD record
ord-0812b3dee8844785bf56f4235189fd74
Source dataset
uspto-grants-1994_07
Patent number
US05331010

Reaction notes

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