Acetaldehyde → 5-(2-Hydroxypropan-1-yl)-2-phenyl-1,3-dioxane

HRID 847002Notes

Reaction equation

HRID 847002 reaction equation
Br[CH2:2][CH:3]1[CH2:8][O:7][CH:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[O:5][CH2:4]1.[Mg].[CH:16](=[O:18])[CH3:17].[Cl-].[NH4+]>O1CCCC1.C(OCC)(=O)C>[OH:18][CH:16]([CH3:17])[CH2:2][CH:3]1[CH2:8][O:7][CH:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[O:5][CH2:4]1

Participants

7

Reactant 4

HCID 177AcetaldehydeHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 148351015-Bromomethyl-2-phenyl-1,3-dioxane

Product 1

HCID 198842565-(2-Hydroxypropan-1-yl)-2-phenyl-1,3-dioxane

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-70 °C

Procedure

To a solution of 19.39 g (75.4 mM) of 5-bromomethyl-2-phenyl-1,3-dioxane m2 in 200 ml of tetrahydrofuran is added 1.923 g (79.17 mM) of magnesium and the mixture is allowed to react for 7 hours under ultrasonic bibration. The mixture is cooled to -70° C. and 21.27 ml (377 mM) of acetaldehyde is added and then the mixture is stirred at 0° C. for 15 hours. The mixture is poured into an ice-cooled saturated aqueous ammonium chloride solution and the product is isolated by ethyl acetate extraction. The ethyl acetate layer is washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and evaporated. By eliminating the polar impurity by passing short column of silica gel, 11.353 g of the crude titled compound m3 is obtained which is used to the next reaction without further purification.

Workup

  1. customto react for 7 hours under ultrasonic bibration
  2. washThe ethyl acetate layer is washed with saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-dc168a8996504b71a0ac9bdb4825a930
Source dataset
uspto-grants-1992_08
Patent number
US05138067

Reaction notes

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