4-Hydroxybenzyl Alcohol → HCID 18621258, compound

HRID 1861685Notes

Reaction equation

HRID 1861685 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.[Cl:10][C:11]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[C:12]=1[CH2:13]Br.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[Cl:10][C:11]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[C:12]=1[CH2:13][O:9][C:6]1[CH:7]=[CH:8][C:3]([CH2:2][OH:1])=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 1254-Hydroxybenzyl AlcoholHCID 10796Cesium carbonateHCID 301591-Bromomethyl-2,6-dichlorobenzene

Product 1

HCID 18621258HCID 18621258, compoundYield 100,710.398%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-(hydroxymethyl)phenol (38.0 g, 0.31 mmol) and 2,6-dichlorobenzyl bromide (73.4 g, 0.31 mmol) in DMF (500 ml) was treated with caesium carbonate (100 g, 0.31 mmol) and heated to 60° for 16 h. The mixture was cooled to room temperature and the solvent evaporated in vacuo. The residue was partitioned between EtOAc (250 ml) and water (250 ml), the aqueous layer was separated and extracted with EtOAc (250 ml) and the combined organic layers washed with 10% hydrochloric acid (100 ml), NaHCO3 solution (100 ml) and brine (200 ml), dried (MgSO4) and the solvent evaporated in vacuo to give the title compound as a brown oil (88.4 g) which was used without further purification. δH (CDCl3) 7.38-7.21 (5H, m, ArH), 7.02 (2H, d, J 8.7 Hz, ArH), 5.28 (2H, s, CH2OAr) and 4.63 (2H, s, CH2OH).

Workup

  1. temperatureheated to 60° for 16 h
  2. customthe solvent evaporated in vacuo
  3. customThe residue was partitioned between EtOAc (250 ml) and water (250 ml)
  4. customthe aqueous layer was separated
  5. extractionextracted with EtOAc (250 ml)
  6. washthe combined organic layers washed with 10% hydrochloric acid (100 ml), NaHCO3 solution (100 ml) and brine (200 ml)
  7. dry with materialdried (MgSO4)
  8. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-def3418f797245388fd5b763be67cf7d
Source dataset
uspto-grants-2003_03
Patent number
US06534513B1

Reaction notes

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