Ethyl Acetate → 2-Benzyloxy-6-methoxybenzyl alcohol

HRID 554543Notes

Reaction equation

HRID 554543 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:14][C:15](=O)[C:16]1[C:21]([O:22][CH3:23])=[CH:20][CH:19]=[CH:18][C:17]=1[O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)C1C=CC=CC=1.C(OCC)(=O)C.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>CCOCC>[CH2:25]([O:24][C:17]1[CH:18]=[CH:19][CH:20]=[C:21]([O:22][CH3:23])[C:16]=1[CH2:15][OH:14])[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 9357Potassium Sodium TartrateHCID 21226445Aluminium lithium hydrideHCID 674612312-Benzyloxy-6-methoxybenzoic Acid Benzyl Ester

Product 1

HCID 674586102-Benzyloxy-6-methoxybenzyl alcoholYield 109.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

In a nitrogen stream, to a suspension of lithium aluminum hydride (0.88 g, 23.14 mmol) in ether (35 mL), a solution of 2-benzyloxy-6-methoxybenzoic acid benzyl ester (6.2 g, 17.80 mmol) in ether (20 mL) was added at room temperature over 15 minutes. The reaction mixture was stirred for two hours under heating to reflux. Ethyl acetate (2 mL) was added dropwise to the reaction mixture under cooling with ice and then a saturated Rochelle salt aqueous solution (20 mL) was added dropwise thereto and the mixture was stirred at room temperature for 20 hours. The reaction mixture was subjected to Celite filtration and to the filtrate was added a saturated Rochelle salt aqueous solution (15 mL) and the mixture was extracted with ether. The organic layer was washed with a saturated sodium chloride aqueous solution and dried (anhydrous sodium sulfate), and then the solvent was distilled under reduced pressure. The obtained residue was purified by silica gel column chromatography [developing solution=ether: n-hexane (1:1)] to obtain the title compound (4.75 g, 100%).

Workup

  1. temperatureunder heating to reflux
  2. temperatureunder cooling with ice
  3. stirringthe mixture was stirred at room temperature for 20 hours
  4. filtrationThe reaction mixture was subjected to Celite filtration and to the filtrate
  5. additionwas added a saturated Rochelle salt aqueous solution (15 mL)
  6. extractionthe mixture was extracted with ether
  7. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  8. dry with materialdried (anhydrous sodium sulfate)
  9. distillationthe solvent was distilled under reduced pressure
  10. customThe obtained residue was purified by silica gel column chromatography [developing solution=ether: n-hexane (1:1)]

Sources & evidence

ORD record
ord-4888bb55093941aeb6134a24ace868b1
Source dataset
uspto-grants-2011_11
Patent number
US08048897B2

Reaction notes

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