Sodium Bisulfate → 4-(Tetrahydropyran-2-yloxy)phenylacetaldehyde
Reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14](O)[CH3:15])=[CH:10][CH:9]=1.S(=O)(=O)(O)[O-:18].[Na+]>C(Cl)Cl>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH:15]=[O:18])=[CH:10][CH:9]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a stirred suspension of 740 g. of Celite diatomaceous earth and 396 g. of chromium trioxide-dipyridine complex (Collins' reagent) in 4 l. of anhydrous methylene chloride, cooled to 0°C is added dropwise a solution of 58 g. of 4-(tetrahydropyran-2-yloxy)phenylethanol in 3 l. of anhydrous methylene chloride, maintaining the temperature of the reaction mixture at 0°-5°C. After completion of the addition, the reaction mixture is stirred for 30 minutes further at 0°C, 396 g. of sodium bisulfate are added and the mixture stirred for 15 additional minutes. It is then filtered through anhydrous magnesium sulfate and evaporated to dryness under reduced pressure, to yield 4-(tetrahydropyran-2-yloxy)phenylacetaldehyde.
Workup
- additionTo a stirred suspension of 740 g
- additionis added dropwise a solution of 58 g
- additionAfter completion of the addition
- stirringthe mixture stirred for 15 additional minutes
- filtrationIt is then filtered through anhydrous magnesium sulfate
- customevaporated to dryness under reduced pressure
Sources & evidence
- ORD record
- ord-f6ecdba02b6349f8b053b8f5548551f0
- Source dataset
- uspto-grants-1976_02
- Patent number
- US03940407
Reaction notes
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