Sodium cyanoborohydride → Methyl 3-(1-Hydroxyethyl)benzoate

HRID 714458Notes

Reaction equation

HRID 714458 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([C:10]([O:12][CH3:13])=[O:11])[CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:2].C([BH3-])#N.[Na+]>CO.Cl>[OH:3][CH:1]([C:4]1[CH:5]=[C:6]([C:10]([O:12][CH3:13])=[O:11])[CH:7]=[CH:8][CH:9]=1)[CH3:2]

Participants

5

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 15094405Methyl 3-acetylbenzoate

Product 1

HCID 20428670Methyl 3-(1-Hydroxyethyl)benzoate

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 887MethanolSolvent

Procedure

1.09 g (6.15 mmol) of methyl 3-acetylbenzenecarboxylate (Example 59A) were initially charged in 28 ml methanol. 0.77 g (12.29 mmol) of sodium cyanoborohydride was added, and the reaction solution was then adjusted to pH 3 using a few drops of 1N hydrochloric acid and stirred at RT overnight. The reaction solution was evaporated, water was then added and the mixture was extracted three times with ethyl acetate. The combined organic phases were dried over magnesium sulfate, filtered and evaporated.

Workup

  1. customThe reaction solution was evaporated
  2. additionwater was then added
  3. extractionthe mixture was extracted three times with ethyl acetate
  4. dry with materialThe combined organic phases were dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-4f6d68fa76cc4e3094b0e29fbb8b8a74
Source dataset
uspto-grants-2015_11
Patent number
US09187428B2

Reaction notes

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