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4-Hydroxybenzaldehyde → 4-[2-(1,3-Dioxan-2-yl)ethoxy]benzaldehyde

HRID 783
Notes
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Reaction equation

HRID 783 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.Br[CH2:11][CH2:12][CH:13]1[O:18][CH2:17][CH2:16][CH2:15][O:14]1.[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C.C(#N)C>[O:14]1[CH2:15][CH2:16][CH2:17][O:18][CH:13]1[CH2:12][CH2:11][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 5206561,3-Dioxane, 2-(2-bromoethyl)-

Product 1

HCID 196934674-[2-(1,3-Dioxan-2-yl)ethoxy]benzaldehydeYield 100.2%

Reagents, catalysts & solvents 2

HCID 6342
Acetonitrile
Solvent
HCID 8857Ethyl AcetateSolvent

Procedure

In a 500 ml flask, 120 ml of acetonitrile, 13.8 g of 4-hydroxybenzaldehyde, 21.1 g of 2-(2-bromoethyl)-1,3-dioxane, 1.8 g of potassium iodide, and 35.8 g of potassium carbonate were placed and then, reacted at 80° C. for 5 hrs. Thereafter, 200 ml of ethyl acetate was added to the reaction mixture and washed once with a saturated aqueous potassium carbonate solution, distilled water, and saturated saline. The washed organic phase was dried over anhydrous magnesium sulfate and removed solvent, to give 25.6 g of 4-(2-[1,3]-dioxane-2-yl-ethoxy)benzaldehyde.

Workup

  1. customreacted at 80° C. for 5 hrs
  2. washwashed once with a saturated aqueous potassium carbonate solution
  3. distillationdistilled water, and saturated saline
  4. dry with materialThe washed organic phase was dried over anhydrous magnesium sulfate
  5. customremoved solvent

Sources & evidence

ORD record
ord-d6f09b988e0848769dd846f380d71108
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05723258

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes