Acetic Acid → HCID 53822308, compound

HRID 865881Notes

Reaction equation

HRID 865881 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-76ff744dd34e42e5b03ef168f0b58953
Source dataset
uspto-grants-1996_10
Patent number
US05567841

Reaction notes

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