3-Hydroxybenzaldehyde → 3-(Morpholinomethyl)phenol

HRID 1981350Notes

Reaction equation

HRID 1981350 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.[NH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1.[BH4-].[Na+]>CO>[O:13]1[CH2:14][CH2:15][N:10]([CH2:5][C:4]2[CH:3]=[C:2]([OH:1])[CH:9]=[CH:8][CH:7]=2)[CH2:11][CH2:12]1

Participants

5

Reactant 3

HCID 1013-HydroxybenzaldehydeHCID 8083MorpholineHCID 4311764Sodium borohydride

Product 1

HCID 132775773-(Morpholinomethyl)phenolYield 67%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 0.2 mol of 3-hydroxybenzaldehyde in 100 ml of methanol, is added, at about 20° C., a solution of 0.4 mol of morpholine in 40 ml of methanol. To the mixture thus obtained is added portionwise, under stirring at the temperature of 20°-25° C. within about 90 minutes, 0.2 mol of sodium borohydride, then the reaction mixture is stirred 3 hours at room temperature and the solvent is evaporated under reduced pressure to dryness. The residue is taken up with ice and acidified with hydrochloric acid, the acid solution is washed twice with 40 ml of ethyl acetate and concentrated ammonium hydroxide is added thereto up to clearly basic reaction. The mixture is extracted 4 times with 80 ml of ethyl acetate and the solvent is evaporated off. The product thus obtained melts at 113°-116° C. Yield: 67%.

Workup

  1. customTo the mixture thus obtained
  2. additionis added portionwise
  3. customthe solvent is evaporated under reduced pressure to dryness
  4. washthe acid solution is washed twice with 40 ml of ethyl acetate and concentrated ammonium hydroxide
  5. additionis added
  6. customup to clearly basic reaction
  7. extractionThe mixture is extracted 4 times with 80 ml of ethyl acetate
  8. customthe solvent is evaporated off

Sources & evidence

ORD record
ord-591820b7973d417e84b2769bedf71645
Source dataset
uspto-grants-1985_04
Patent number
US04514408

Reaction notes

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