Water → HCID 61669341, compound

HRID 591745Notes

Reaction equation

HRID 591745 reaction equation
[OH:1][C:2]1[C:9]([CH3:10])=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[CH3:11].Br[CH2:13][CH2:14][CH2:15][CH2:16][OH:17].C([O-])([O-])=O.[Cs+].[Cs+].O>CN(C=O)C>[OH:17][CH2:16][CH2:15][CH2:14][CH2:13][O:1][C:2]1[C:3]([CH3:11])=[CH:4][C:5]([CH:6]=[O:7])=[CH:8][C:9]=1[CH3:10]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 752223,5-Dimethyl-4-hydroxybenzaldehydeHCID 1183884-Bromobutanol

Product 1

HCID 61669341HCID 61669341, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-hydroxy-3,5-dimethyl benzaldehyde (5.00 g, 33.3 mmol) in DMF (30 mL) were added 4-bromo-butan-1-ol (6.11 g, 39.9 mmol) and Cs2CO3 (16.2 g, 50.0 mmol). The reaction mixture was stirred at room temperature for 48 hours, then water (100 mL) was added, and the products were extracted with ethyl acetate (2×200 mL). The combined organic phase was washed with water (100 mL), then brine (100 mL), and dried over anhydrous Na2SO4. Solvent was removed and the crude product was purified by the Simpliflash system, using 40% ethyl acetate in hexane as eluent, to give 4-(4-hydroxybutoxy)-3,5-dimethyl benzaldehyde as a colorless liquid. Yield: 0.66 g (7%).

Workup

  1. extractionthe products were extracted with ethyl acetate (2×200 mL)
  2. washThe combined organic phase was washed with water (100 mL)
  3. dry with materialbrine (100 mL), and dried over anhydrous Na2SO4
  4. customSolvent was removed
  5. customthe crude product was purified by the Simpliflash system

Sources & evidence

ORD record
ord-83d4e45d68184bd7942810a3db57c6f2
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

Loading…