Hydrochloric Acid → 4-(2-Benzyloxybenzyl)benzyl alcohol

HRID 1982810Notes

Reaction equation

HRID 1982810 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([O:14][C:15]1[CH:31]=[CH:30][CH:29]=[CH:28][C:16]=1[CH2:17][C:18]1[CH:27]=[CH:26][C:21]([C:22](OC)=[O:23])=[CH:20][CH:19]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(OCC)(=O)C.Cl>O1CCCC1.O>[CH2:7]([O:14][C:15]1[CH:31]=[CH:30][CH:29]=[CH:28][C:16]=1[CH2:17][C:18]1[CH:19]=[CH:20][C:21]([CH2:22][OH:23])=[CH:26][CH:27]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 21909320Methyl 4-(2-benzyloxybenzyl)benzoate

Product 1

HCID 688722414-(2-Benzyloxybenzyl)benzyl alcoholYield 98.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of lithium aluminum hydride (0.47 g) in tetrahydrofuran (5 mL) was added dropwise a solution of methyl 4-(2-benzyloxybenzyl)benzoate (2.1 g) in tetrahydrofuran (5 mL) at 0° C. After the mixture was stirred at the same temperature for 1 hour, to the mixture was added ethyl acetate, and the mixture was stirred for additional 30 minutes. To the reaction mixture were added water and dilute hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to give 4-(2-benzyloxybenzyl)benzyl alcohol (1.9 g).

Workup

  1. stirringthe mixture was stirred for additional 30 minutes
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-dcbe66cf081840abafed63fac05a25f0
Source dataset
uspto-grants-2009_06
Patent number
US07541341B2

Reaction notes

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