Hydrochloric Acid → (4-Bromo-benzyloxy)-acetaldehyde

HRID 2219220Notes

Reaction equation

HRID 2219220 reaction equation
Cl.[Br:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][O:10][CH2:11][CH:12](OCC)[O:13]CC)=[CH:5][CH:4]=1>C(OCC)C.[Cl-].[Na+].O>[Br:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][O:10][CH2:11][CH:12]=[O:13])=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58816128HCID 58816128, compound

Product 1

HCID 10868072(4-Bromo-benzyloxy)-acetaldehyde

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

5 N HCl (20 mL) is added to a stirred solution of 1-bromo 4-(2,2-diethoxy-ethoxymethyl)-benzene (1.86 g, 6.13 mmol) in diethyl ether (20 mL) at ambient temperature. The resultant two-layered mixture is stirred vigorously under nitrogen for 16 hours. Diethyl ether (30 mL) and brine (20 mL) are added to the mixture. The organic layer is separated, washed with half-saturated brine, dried, filter and concentrated into a ˜50 mL solution (35 mg/mL). 1H NMR (CDCl3): δ9.72 (s, 1H), 7.49 (d, J=7.49 Hz, 2H), 7.24 (d, J=7.9 Hz, 2H), 4.57 (s, 2H), 4.11 (s, 2H).

Workup

  1. customThe organic layer is separated
  2. washwashed with half-saturated brine
  3. customdried
  4. filtrationfilter
  5. concentrationconcentrated into a ˜50 mL solution (35 mg/mL)

Sources & evidence

ORD record
ord-ddb3da2065374c6896e42bddf45ceebd
Source dataset
uspto-grants-2008_08
Patent number
US07414063B2

Reaction notes

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