Methanol → 2-diallylaminomethyl-phenol

HRID 1885021Notes

Reaction equation

HRID 1885021 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[CH2:10]([NH:13][CH2:14][CH:15]=[CH2:16])[CH:11]=[CH2:12].CO.[BH4-].[Na+]>O>[CH2:10]([N:13]([CH2:4][C:3]1[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=1[OH:1])[CH2:14][CH:15]=[CH2:16])[CH:11]=[CH2:12]

Participants

6

Reactant 4

HCID 887MethanolHCID 6998SalicylaldehydeHCID 31279DiallylamineHCID 4311764Sodium borohydride

Product 1

HCID 40347872-diallylaminomethyl-phenolYield 64%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

12 g of 2-hydroxybenzaldehyde was placed in a 500 ml round bottom flask with 100 ml of diallyl amine and 100 ml of methanol. The reaction mixture was then cooled to 0° C. 4 g of NaBH4 (powder) was slowly added within 2.5 hrs and the temperature was kept at 0-6° C. Water was then added to the reaction mixture to terminate the reaction. The reaction mixture was then concentrated, and extracted with ethyl acetate and water. The organic phase was collected and concentrated to obtain crude product. The obtained crude product was eluted and purified with mobile phase eluant of n-hexane:ethylacetate (EA)=4: 1 and solid phase of silica gel. 12.8 g of the product of formula (IX) was obtained and recovery yield was 64%.

Workup

  1. customwas kept at 0-6° C
  2. customto terminate
  3. customthe reaction
  4. concentrationThe reaction mixture was then concentrated
  5. extractionextracted with ethyl acetate and water
  6. customThe organic phase was collected
  7. concentrationconcentrated
  8. customto obtain crude product
  9. customThe obtained crude product
  10. washwas eluted
  11. custompurified with mobile phase eluant of n-hexane

Sources & evidence

ORD record
ord-3a0e2a6006804048a677ff0834e4a0e0
Source dataset
uspto-grants-2004_07
Patent number
US06767970B2

Reaction notes

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