3-Benzyloxybenzaldehyde → 3-(Phenylmethoxy)benzenemethanol

HRID 1484087Notes

Reaction equation

HRID 1484087 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[CH:12]=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[Ca+2].[Cl-].[BH4-].[Na+]>C(O)C.C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:12][OH:13])[CH:14]=[CH:15][CH:16]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 743423-BenzyloxybenzaldehydeHCID 4311764Sodium borohydrideHCID 5284359Calcium Chloride

Product 1

HCID 743413-(Phenylmethoxy)benzenemethanolYield 81.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

The intermediate 33 (8.2 mmols) and calcium chloride (16.4 mmols) were dissolved in 55 mL of anhydrous ethanol and 27 mLs of THF. The solution was next cooled to 0° C. and sodium borohydride (16.4 mmols) was added slowly over several minutes to the reaction vessel. Upon warming to ambient temperature, the mixture was allowed to stir for an additional 15 hours. After this time, the flask was again cooled to 0° C. and the excess sodium borohydride was quenched with the addition of 5 mLs of 1N HCl. The aqueous layer was extracted with four 20 mL portions of EtOAc; the organic layers were then combined, washed with 10 mLs of brine and dried with MgSO4. After evaporation, the crude organic material was purified by flash chromatography and 6.7 mmols of the title product was recovered. 1H NMR (300 MHz, CDCl3) δ 7.49-7.24 (m, 5H), 7.06-6.88 (m, 2H), 5.08 (s, 21-1), 4.66 (s, 2H), 1.78 (s, 1H). 13C NMR (75 MHz, CDCl3) δ 129.88, 128.83, 128.21, 127.72, 119.60, 114.35, 113.45, 70.17, 65.46.

Workup

  1. temperatureUpon warming to ambient temperature
  2. temperatureAfter this time, the flask was again cooled to 0° C.
  3. customthe excess sodium borohydride was quenched with the addition of 5 mLs of 1N HCl
  4. extractionThe aqueous layer was extracted with four 20 mL portions of EtOAc
  5. washwashed with 10 mLs of brine
  6. dry with materialdried with MgSO4
  7. customAfter evaporation

Sources & evidence

ORD record
ord-7c85073384234e75a9c7fe3407284686
Source dataset
uspto-grants-2016_08
Patent number
US09421177B2

Reaction notes

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