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

HRID 1385906Notes

Reaction equation

HRID 1385906 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 dry 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, the solution was 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)benzyl alcohol 13.56 g as a yellow oil. The crude product thus obtained of α-(3-cyclopentyloxy-4-methoxyphenyl)benzyl alcohol in an amount of 10.00 g was dissolved in dry methylene chloride (110 ml), manganese dioxide (16.00 g) was added to the solution, and the solution was vigorously stirred at room temperature for 2 days. The undissolved material in the solution obtained were 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 with 20% ethyl acetate/hexane). The solvent was removed in vacuo and the 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-362d947d2ccc4155b8f86d6a7a982c5d
Source dataset
uspto-grants-2001_07
Patent number
US06265402B1

Reaction notes

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