3-Hydroxybenzyl alcohol → HCID 59612676, compound

HRID 1808729Notes

Reaction equation

HRID 1808729 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.[CH3:10]C1C=CC(S(O)(=O)=O)=CC=1.[C:21]([O-:24])([O-])=O.[K+].[K+].[Br:27][CH2:28][CH2:29][CH2:30]Br>C(O)CO>[Br:27][CH2:28][CH2:29][CH2:30][O:9][C:5]1[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=1)[CH2:2][O:1][CH2:10][CH2:21][OH:24]

Participants

6

Reactant 4

HCID 1023-Hydroxybenzyl alcoholHCID 6101p-Toluenesulfonic acidHCID 80011,3-DibromopropaneHCID 11430Potassium Carbonate

Product 1

HCID 59612676HCID 59612676, compound

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Conditions

Temperature
80 °C

Procedure

The solution of 3-(hydroxymethyl)phenol (8.8 g, 71 mmol) and of paratoluenesulfonic acid (PTSA) (2.3 g, 13.4 mmol) in ethylene glycol (180 mL) is heated to 130° C. under argon for 40 hrs. After cooling down to 80° C., K2CO3 (13 g, 94 mmol) and then 1,3-dibromopropane (42 mL, 386 mmol) are added. After 2 hrs of stirring at this temperature, the reaction is cooled to RT and extracted with a DCM-H2O mixture. And then the organic phase is washed several times with water, dried on Na2SO4 and concentrated in vacuo. The final crude product is obtained as a yellow oil (14 g, 68% for two steps) and used without any further purification.

Workup

  1. temperaturethe reaction is cooled to RT
  2. extractionextracted with a DCM-H2O mixture
  3. washAnd then the organic phase is washed several times with water
  4. customdried on Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-92ac93fbb546464f92e377e0859d5c7a
Source dataset
uspto-grants-2013_01
Patent number
US08361993B2

Reaction notes

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