Hydrochloric Acid → 3-Cyclopentyloxy-4-methoxybenzyl alcohol

HRID 1244878Notes

Reaction equation

HRID 1244878 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:7]1([O:12][C:13]2[CH:14]=[C:15]([CH:18]=[CH:19][C:20]=2[O:21][CH3:22])[CH:16]=[O:17])[CH2:11][CH2:10][CH2:9][CH2:8]1.Cl>C1COCC1>[CH:7]1([O:12][C:13]2[CH:14]=[C:15]([CH2:16][OH:17])[CH:18]=[CH:19][C:20]=2[O:21][CH3:22])[CH2:8][CH2:9][CH2:10][CH2:11]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 27358933-Cyclopentyloxy-4-methoxybenzaldehydeHCID 21226445Aluminium lithium hydride

Product 1

HCID 111387063-Cyclopentyloxy-4-methoxybenzyl alcoholYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1M lithium aluminum hydride in THF (1.5 mL) was added into a stirred solution of 3-cyclopentyloxy-4-methoxybenzaldehyde (1.1 g; 5 mmol) in THF solution in an ice bath. After the reaction was completed (as evidenced by TLC), the mixture was acidified with 2M HCl and extracted with ether. The organic phase was washed with water and dried over MgSO4. Filtration, followed by evaporation gave (3-cyclopentyloxy-4-methoxyphenyl)methanol as an oil ( 0.9 g; 81% yield; purity 98.1% by HPLC area). 1H-NMR: 6.92 (s, 1H), 6.88 (d, J=8.2 Hz, 1H), 6.84 (d, J=8.1 Hz, 1H), 4.80 (m, 1H), 4.61 (s, 2H), 3.84 (s, 3H), 2.13–1.78 (m, 6H), and 1.61 (s, 2H). 13C-NMR: 149.4, 147.6, 133.6, 119.3, 114.0, 111.7, 80.3, 60.5, 56.0, 32.7, and 24.0.

Workup

  1. extractionextracted with ether
  2. washThe organic phase was washed with water
  3. dry with materialdried over MgSO4
  4. filtrationFiltration
  5. customfollowed by evaporation

Sources & evidence

ORD record
ord-e6d96012981e4ee7898a9f5e2e06cc83
Source dataset
uspto-grants-2006_10
Patent number
US07122705B2

Reaction notes

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