Water → HCID 61669147, compound

HRID 591736Notes

Reaction equation

HRID 591736 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][OH:16].C([O-])([O-])=O.[Cs+].[Cs+].O>CN(C=O)C>[OH: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 123083-Bromo-1-propanolHCID 752223,5-Dimethyl-4-hydroxybenzaldehyde

Product 1

HCID 61669147HCID 61669147, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-hydroxy-3,5-dimethyl benzaldehyde (5.0 g, 33.29 mmol) in DMF (30 mL) were added 3-bromo propan-1-ol (5.56 g, 39.95 mmol) and Cs2CO3 (16.24 g, 50.0 mmol). Then, the reaction mixture was stirred at room temperature for 48 hours. Then, water was added and the products were extracted with ethyl acetate (2×250 mL). The combined organic phase was washed with water (100 mL), then brine (100 mL), and dried over anhydrous Na2SO4. Removal of solvent gave 4-(3-hydroxypropoxy)-3,5-dimethyl benzaldehyde as a colorless liquid. Yield: 5.38 g (77%).

Workup

  1. extractionthe products were extracted with ethyl acetate (2×250 mL)
  2. washThe combined organic phase was washed with water (100 mL)
  3. dry with materialbrine (100 mL), and dried over anhydrous Na2SO4
  4. customRemoval of solvent

Sources & evidence

ORD record
ord-57ab9ec8a4264387908db03ca557c242
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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