Sodium borohydride → (4-(3-(Trifluoromethyl)phenoxy)phenyl)methanol

HRID 536169Notes

Reaction equation

HRID 536169 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:4]=[C:5]([O:9][C:10]2[CH:17]=[CH:16][C:13]([CH:14]=[O:15])=[CH:12][CH:11]=2)[CH:6]=[CH:7][CH:8]=1.[BH4-].[Na+]>CO>[F:1][C:2]([F:18])([F:19])[C:3]1[CH:4]=[C:5]([O:9][C:10]2[CH:17]=[CH:16][C:13]([CH2:14][OH:15])=[CH:12][CH:11]=2)[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 121487884-(3-(Trifluoromethyl)phenoxy)benzaldehyde

Product 1

HCID 66825531(4-(3-(Trifluoromethyl)phenoxy)phenyl)methanolYield 121.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-{[3-(Trifluoromethyl)phenyl]oxy}benzaldehyde (4.1 g, 9.55 mmol) in methanol (50 mL) at 0° C. was added sodium borohydride (1.0 g, 26.4 mmol) in portions. The reaction mixture was allowed to warm to rt and stirred for 1 h, then quenched with acetone, concentrated. Purification via ISCO system afforded the title product (3.11 g) as a colorless liquid. LC-MS (ESI): m/z 251 [M-OH]+; 3.23 min (ret time).

Workup

  1. customquenched with acetone
  2. concentrationconcentrated
  3. customPurification via ISCO system

Sources & evidence

ORD record
ord-7412d11c45af43de87020817d2bfe525
Source dataset
uspto-grants-2014_10
Patent number
US08859573B2

Reaction notes

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