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

HRID 2355362Notes

Reaction equation

HRID 2355362 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-1e7bceab2a0841f3b7b3a470295b0943
Source dataset
uspto-grants-2010_07
Patent number
US07754737B2

Reaction notes

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