3-Hydroxybenzyl alcohol → HCID 59612661, compound

HRID 1808727Notes

Reaction equation

HRID 1808727 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4]Br.C([O-])([O-])=O.[K+].[K+].[OH:12][CH2:13][C:14]1[CH:15]=[C:16]([OH:20])[CH:17]=[CH:18][CH:19]=1.CCOCC>CN(C)C=O>[Br:1][CH2:2][CH2:3][CH2:4][O:20][C:16]1[CH:15]=[C:14]([CH2:13][OH:12])[CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 1023-Hydroxybenzyl alcoholHCID 3283Diethyl EtherHCID 80011,3-DibromopropaneHCID 11430Potassium Carbonate

Product 1

HCID 59612661HCID 59612661, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

1,3-dibromopropane (23 mL, 0.22 mol) is gradually added to a suspension of K2CO3 (3.2 g, 23 mmol) and 3-(hydroxymethyl)phenol (5 g, 40.3 mmol) in dimethylformamide (DMF) (30 mL) stirred beforehand for 5 min at 65° C. The reaction medium is maintained under stirring for 45 min at the same temperature. After cooling to room temperature (RT), Et2O (150 mL) is added and the organic phase is extracted 4 times with a saturated NaCl aqueous solution. The organic phase is dried on Na2SO4. After evaporation of the solvent under reduced pressure, a viscous colorless oil is obtained (6.7 g, 68%) which gradually crystallizes.

Workup

  1. temperatureThe reaction medium is maintained
  2. stirringunder stirring for 45 min at the same temperature
  3. additionis added
  4. extractionthe organic phase is extracted 4 times with a saturated NaCl aqueous solution
  5. customThe organic phase is dried on Na2SO4
  6. customAfter evaporation of the solvent under reduced pressure
  7. customa viscous colorless oil is obtained (6.7 g, 68%) which
  8. customgradually crystallizes

Sources & evidence

ORD record
ord-35847752b202420395641bc851381176
Source dataset
uspto-grants-2013_01
Patent number
US08361993B2

Reaction notes

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