3-Hydroxybenzaldehyde → 3-(Pyrrolidin-1-ylmethyl)phenol

HRID 1493175Notes

Reaction equation

HRID 1493175 reaction equation
[BH4-].[Na+].[OH:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=O.[NH:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1>C(O)C>[N:12]1([CH2:7][C:6]2[CH:5]=[C:4]([OH:3])[CH:11]=[CH:10][CH:9]=2)[CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 1013-HydroxybenzaldehydeHCID 31268PyrrolidineHCID 4311764Sodium borohydride

Product 1

HCID 8707853-(Pyrrolidin-1-ylmethyl)phenol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (15.2 g) was added to a solution of 3-hydroxybenzaldehyde (48.8 g) and pyrrolidine (66.4 ml) in ethanol. After 18 hours the ethanol was removed and the residual oil was acidified with hydrochloric acid and washed with ethyl acetate. The aqueous solution was then basified with ammonia and extracted with ethyl acetate. Evaporation of the organic extracts yielded the title compound as an off-white solid (21.4 g), m.p. 100°-102°. TLC Silica; methanol; 0.88 ammonia (80:1)Rf 0.48.

Workup

  1. customAfter 18 hours the ethanol was removed
  2. washwashed with ethyl acetate
  3. extractionextracted with ethyl acetate
  4. customEvaporation of the organic extracts

Sources & evidence

ORD record
ord-0d69d884b5d04712904d50010c471593
Source dataset
uspto-grants-1991_06
Patent number
US05021429

Reaction notes

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