Sodium Hydroxide → 2-(2,6-Dibromophenyl)-1,3-dioxane

HRID 1918431Notes

Reaction equation

HRID 1918431 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([Br:10])[C:3]=1[CH:4]=[O:5].[CH:11](O)([OH:14])[CH2:12][CH3:13].C(OC(OCC)OCC)C.[OH-].[Na+]>C(Cl)Cl.[Cl-].[Cl-].[Cl-].[Cl-].[Zr+4]>[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([Br:10])[C:3]=1[CH:4]1[O:14][CH2:11][CH2:12][CH2:13][O:5]1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 31214Ethyl orthoformateHCID 134919PropanediolHCID 126486412,6-Dibromobenzaldehyde

Product 1

HCID 688620862-(2,6-Dibromophenyl)-1,3-dioxaneYield 98%

Reagents, catalysts & solvents 2

HCID 9856075Zirconium chloride (ZrCl4), (T-4)-CatalystHCID 6344DichloromethaneSolvent

Procedure

2,6-Dibromobenzaldehyde (49) (10.0 g, 37.9 mmol) was dissolved in 160 ml dry CH2Cl2. Propanediol (6.4 ml, 88.5 ml), triethylorthoformate (6.83 ml, 41 mmol) and anhydrous ZrCl4 (1.0 g) were added at ambient temperature and stirred overnight. Then NaOH (50 ml of a 10% solution) was added and stirred for an additional hour. The organic phase was separated, the aqueous phase was extracted with Et2O (2×40 ml). The combined organic phases were washed with water (3×60 ml), dried over MgSO4 and the volatiles were removed in vacuo to afford 12 g (98%) 2-(2,6-Dibromophenyl)-1,3-dioxane (acetal) as a slightly yellow solid.

Workup

  1. stirringstirred for an additional hour
  2. customThe organic phase was separated
  3. extractionthe aqueous phase was extracted with Et2O (2×40 ml)
  4. washThe combined organic phases were washed with water (3×60 ml)
  5. dry with materialdried over MgSO4
  6. customthe volatiles were removed in vacuo

Sources & evidence

ORD record
ord-54b4e776df9c443ca3f226877d2e50f3
Source dataset
uspto-grants-2013_12
Patent number
US08618328B2

Reaction notes

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