Sodium borohydride → HCID 54420115, compound

HRID 868282Notes

Reaction equation

HRID 868282 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 solution 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 solution 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-a74598494e4045cbbd079c7c74d431d3
Source dataset
uspto-grants-1988_10
Patent number
US04778818

Reaction notes

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