Sodium borohydride → HCID 54420115, compound

HRID 1789003Notes

Reaction equation

HRID 1789003 reaction equation
[BH4-].[Na+].[CH:3]([C:5]1[CH:22]=[CH:21][CH:20]=[CH:19][C:6]=1[CH:7]=[CH:8][CH2:9][C:10]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:11]=1[OH:18])=[O:4]>CO>[OH:4][CH2:3][C:5]1[CH:22]=[CH:21][CH:20]=[CH:19][C:6]=1[CH:7]=[CH:8][CH2:9][C:10]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:11]=1[OH:18]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 53656210HCID 53656210, compound

Product 1

HCID 54420115HCID 54420115, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (35 mg) was added in one portion to a solution of 2-(o-formylcinnamyl)-4-methoxyphenol (240 mg; 0.89 mM) in 5 ml of methanol. The reaction was stirred at room temperature for 2 hours and then the solvent was removed in vacuo. The residue was taken up in 2N aqueous hydrochloric acid and extracted with ether. The ethereal phase was washed with water, dried over magnesium sulfate, stripped of solvent, and filtered through 11/2" of silica gel in a 30 ml fritted funnel with 100 ml of 50% ethyl acetate/hexane providing 240 mg (99%) of pure 2-(o-hydroxymethylcinnamyl)-4-methoxyphenol.

Workup

  1. customthe solvent was removed in vacuo
  2. extractionextracted with ether
  3. washThe ethereal phase was washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered through 11/2" of silica gel in a 30 ml fritted funnel with 100 ml of 50% ethyl acetate/hexane providing 240 mg (99%) of pure 2-(o-hydroxymethylcinnamyl)-4-methoxyphenol

Sources & evidence

ORD record
ord-574d169d1775494e8913267252cbb8a4
Source dataset
uspto-grants-1987_08
Patent number
US04686235

Reaction notes

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