Hydrochloric Acid → Acetaldehyde, 2-(4-bromo-2-methylphenoxy)-

HRID 2219229Notes

Reaction equation

HRID 2219229 reaction equation
Cl.[Br:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH2:10][CH:11](OC)[O:12]C)=[C:5]([CH3:16])[CH:4]=1.[Na+].[Cl-]>CCOCC>[Br:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH2:10][CH:11]=[O:12])=[C:5]([CH3:16])[CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 196085464-Bromo-1-[(2,2-dimethoxyethyl)oxy]-2-methylbenzene

Product 1

HCID 14816015Acetaldehyde, 2-(4-bromo-2-methylphenoxy)-Yield 116.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A 5N HCl (15 mL) solution is added to a stirred solution of 4-bromo-1-(2,2-dimethoxy-ethoxy)-2-methyl-benzene (1.40 g, 5.09 mmol) in Et2O (25 mL). The two-layered solution is stirred vigorously at ambient temperature under nitrogen for 2 days. Et2O (50 mL) and saturated aqueous NaCl solution (25 mL) are added to the mixture. The organic layer is separated, washed with a half-saturated aqueous NaCl solution (30 mL) containing saturated NaHCO3 (0.5 mL), dried over MgSO4, filtered and concentrated at ambient temperature to give 1.36 g of the crude (4-bromo-2-methyl-phenoxy)acetaldehyde as oil. The oil is diluted in Et2O to form a stock solution (67 mg/mL), which is used for the subsequent reaction.

Workup

  1. customThe organic layer is separated
  2. washwashed with a half-saturated aqueous NaCl solution (30 mL)
  3. additioncontaining saturated NaHCO3 (0.5 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated at ambient temperature

Sources & evidence

ORD record
ord-36d53961a31b4a5580efbc5935d2a03d
Source dataset
uspto-grants-2008_08
Patent number
US07414063B2

Reaction notes

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