Acetic Acid → HCID 53822308, compound

HRID 727515Notes

Reaction equation

HRID 727515 reaction equation
[BH4-].[Na+].[O:3]([C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=1)[CH:13]=O)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:18]([OH:21])(=O)[CH3:19].[CH3:22]O>>[O:3]([C:10]1[CH:11]=[C:12]([CH2:13][CH2:22][CH2:19][CH2:18][OH:21])[CH:15]=[CH:16][CH:17]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 382843-PhenoxybenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 53822308HCID 53822308, compoundYield 100%

Procedure

Sodium borohydride (961 mg, 25.3 mmol) was added in one portion to a solution of 3-phenoxybenzaldehyde (10.0 g, 50.5 mmol) in methanol (150 mL) at RT under argon. Once the bubbling ceased, the reaction was stirred at RT for 5 min, then adjusted to pH 6 with glacial acetic acid (about 1 mL). The reaction was concentrated in vacuo to give a residue, which was partitioned between EtOAc (200 mL) and saturated NaHCO3 (50 mL). The organic layer was washed with water and brine (50 mL each), then dried over MgSO4. Evaporation gave title compound (10.1 g, 100%) as a tan oil.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customto give a residue, which
  3. customwas partitioned between EtOAc (200 mL) and saturated NaHCO3 (50 mL)
  4. washThe organic layer was washed with water and brine (50 mL each)
  5. dry with materialdried over MgSO4
  6. customEvaporation

Sources & evidence

ORD record
ord-6848f07bee1a40df9f527a334d3e84b1
Source dataset
uspto-grants-1998_01
Patent number
US05712396

Reaction notes

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