Hydrochloric Acid → [2-(3-Methoxybenzyl)cyclohexyl]methanol

HRID 2389374Notes

Reaction equation

HRID 2389374 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:22]=[CH:23][CH:24]=1)[CH2:12][CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]1[C:19](O)=[O:20].Cl>C1COCC1.O>[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:22]=[CH:23][CH:24]=1)[CH2:12][CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]1[CH2:19][OH:20]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 19358413HCID 19358413, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 68533760[2-(3-Methoxybenzyl)cyclohexyl]methanolYield 80.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
60 °C

Procedure

Under N2 gas atmosphere, to a stirred mixture of lithium aluminum hydride (0.703 g) in THF (9 mL) was added 2-(3-methoxybenzyl)cyclohexanecarboxylic acid (2.3 g) in THF (9 mL) dropwise at 0° C. The reaction mixture was stirred at 0° C. for an hour, at ambient temperature for an hour, at 60° C. for 4 hours. The reaction mixture was cooled to 0° C. and was added mixed solution (1M HCl aqueous solution:THF=10:90) dropwise. The resulting mixture was diluted with water and was extracted with diethylether two times. The organic layer was dried over anhydrous MgSO4, filtered and evaporated in vacuo. The mixture was purified by thin-layer chromatography (n-hexane:EtOAc=5:1) to give [2-(3-methoxybenzyl)cyclohexyl]methanol (1.74 g) as a pale yellow oil.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. additionwas added
  3. extractionwas extracted with diethylether two times
  4. dry with materialThe organic layer was dried over anhydrous MgSO4
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe mixture was purified by thin-layer chromatography (n-hexane:EtOAc=5:1)

Sources & evidence

ORD record
ord-399a25e4469b4631bbdec8bb02b95d6c
Source dataset
uspto-grants-2012_09
Patent number
US08273745B2

Reaction notes

Loading…