Sodium borohydride → Ethyl 3-(hydroxy(phenyl)methyl)benzoate

HRID 1254242Notes

Reaction equation

HRID 1254242 reaction equation
[C:1]([C:9]1[CH:10]=[C:11]([CH:17]=[CH:18][CH:19]=1)[C:12]([O:14][CH2:15][CH3:16])=[O:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>C(O)C>[OH:8][CH:1]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:9]1[CH:10]=[C:11]([CH:17]=[CH:18][CH:19]=1)[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 14789261Ethyl 3-benzoylbenzoate

Product 1

HCID 57544858Ethyl 3-(hydroxy(phenyl)methyl)benzoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 3-benzoylbenzoate (1.0197 g, 4.0 mmol, 1.0 equiv) in ethanol (10 mL) was added of NaBH4 (0.32 g, 2.1 equiv). The reaction mixture was stirred at rt for 1.5 h, quenched with 10% aq Na2CO3, extracted three times with CH2Cl2, and dried over Na2SO4. The crude product was used in the next step without further purification. LC-MS (3 min) tR=1.64 min, m/z 239 (M+-OH). 1H NMR (400 MHz, CDCl3) δ 8.09 (m, 1H), 7.93-7.96 (m, 1H), 7.56-7.59 (m, 1H), 7.26-7.43 (m, 6H), 5.89 (s, 1H), 4.36 (q, J=7.2 Hz, 2H), 2.38 (br s, 1H), 1.40 (t, J=7.2 Hz, 3H).

Workup

  1. customquenched with 10% aq Na2CO3
  2. extractionextracted three times with CH2Cl2
  3. dry with materialdried over Na2SO4
  4. customThe crude product was used in the next step without further purification
  5. customLC-MS (3 min) tR=1.64 min, m/z 239 (M+-OH)

Sources & evidence

ORD record
ord-4c4a669df9ce4d91baa0472c6a282894
Source dataset
uspto-grants-2013_06
Patent number
US08455521B2

Reaction notes

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