Hydrochloric Acid → 2-(2-Chlorophenyl)acetaldehyde

HRID 1502396Notes

Reaction equation

HRID 1502396 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]=[CH:9][O:10]C.Cl.C(=O)(O)[O-].[Na+]>O1CCOCC1.C(OCC)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH:9]=[O:10]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 541782831-Chloro-2-(2-methoxyvinyl)benzene

Product 1

HCID 113786242-(2-Chlorophenyl)acetaldehydeYield 92.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 1-chloro-2-(2-methoxyvinyl)benzene (2.4 g, 14 mmol) in a solution of 4.0M hydrogen chloride in 1,4-dioxane (36 mL) was stirred for 30 minutes at room temperature. The reaction mixture was then diluted with diethyl ether (100 mL) and treated with saturated aqueous sodium bicarbonate solution (60 mL)—caution: gas evolution. The organic layer was separated, washed with a sodium phosphate buffer (1.0M solution in water, pH=8, 2×40 mL), dried over sodium sulfate, filtered, and evaporated in vacuo to afford the title compound as a colorless oil (2.0 g, 90%), which was used in the next step without further purification.

Workup

  1. customThe organic layer was separated
  2. washwashed with a sodium phosphate buffer (1.0M solution in water, pH=8, 2×40 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-fca9cbd2cbe6494cb3a775a7c482b079
Source dataset
uspto-grants-2015_12
Patent number
US09206175B2

Reaction notes

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