Sodium borohydride → HCID 11437583, compound

HRID 1501086Notes

Reaction equation

HRID 1501086 reaction equation
[BH4-].[Na+].[C:3]([C:11]1[CH:23]=[CH:22][C:14]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[CH:13][CH:12]=1)(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C(O)C>[OH:10][CH:3]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)[C:11]1[CH:12]=[CH:13][C:14]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 22163394HCID 22163394, compound

Product 1

HCID 11437583HCID 11437583, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (1.04 g, 27.4 mmol) was added to the solution of tert-butyl 4-benzoylbenzoate (1.54 g, 5.46 mmol) in ethanol (50 mL). Then the mixture was stirred at room temperature for 2 hours. The resultant mixture was concentrated to give a residue. The residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=3:1) to give tert-butyl 4-(hydroxy(phenyl)methyl)benzoate (1.55 g, 100%). 1H NMR (300 MHz, d6-DMSO): δ 7.82 (d, J=8.1 Hz, 2H), 7.48 (d, J=8.1 Hz, 2H), 7.36-7.26 (m, 4H), 7.22-7.17 (m, 1H), 6.04 (d, J=3.9 Hz, 1H), 5.76 (d, J=3.9 Hz, 1H), 1.52 (s, 9H).

Workup

  1. concentrationThe resultant mixture was concentrated
  2. customto give a residue
  3. customThe residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=3:1)

Sources & evidence

ORD record
ord-f56b1146ab5041508c6f2a994aa27db9
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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