Water → alpha-(3-Cyclopentyloxy-4-methoxyphenyl)benzylalcohol

HRID 1068577Notes

Reaction equation

HRID 1068577 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:12]=[CH:13][C:14]=2[O:15][CH3:16])[CH:10]=[O:11])[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:17]1(C)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C1([Li])C=CC=CC=1.O>O1CCCC1>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:10]([OH:11])[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:12]=[CH:13][C:14]=2[O:15][CH3:16])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 27358933-Cyclopentyloxy-4-methoxybenzaldehydeHCID 178506676HCID 178506676, compound

Product 1

HCID 10565992alpha-(3-Cyclopentyloxy-4-methoxyphenyl)benzylalcohol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-cyclopentyloxy-4-methoxybenzaldehyde (10.00 g, 45.40 mM) in dried tetrahydrofuran (50 ml) was cooled to −78° C. A toluene solution of phenyllithium (49.94 mM) was dropped into this solution and the resultant mixture was stirred at that temperature for 5 hours. Water was added to the solution obtained, which was then warmed to room temperature and extracted with diethyl ether. The extract was dried over anhydrous magnesium sulfate, then the solvent was removed in vacuo to obtain a crude product of α-(3-cyclopentyloxy-4-methoxyphenyl)benzylalcohol (13.56 g) as a yellow oil. The crude product (10.00 g) of α-(3-cyclopentyloxy-4-methoxyphenyl)benzylalcohol was dissolved in dried methylene chloride (110 ml) thus obtained, manganese dioxide (16.00 g) was added to the solution, then the solution was vigorously stirred at room temperature for 2 days. The undissolved material in the solution was removed by filtration through Celite and the filtrate was concentrated in vacuo to obtain a residue as a yellow solid. The residue was purified by flash chromatography (SiO2: eluted by 20% ethyl acetate/hexane). The solvent was removed in vacuo and the resultant product was dried to obtain 3-cyclopentyloxy-4-methoxybenzophenone 9.20 g (yield 92.6%) as a light yellow solid.

Workup

  1. customobtained
  2. extractionextracted with diethyl ether
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-980a1959469e4e74a0d1e029928537bb
Source dataset
uspto-grants-2001_06
Patent number
US06251897B1

Reaction notes

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