Dihydrobenzofuran → 2,3-Dihydrobenzofuran-5-carboxaldehyde

HRID 1275971Notes

Reaction equation

HRID 1275971 reaction equation
[CH3:1][O:2][CH:3](Cl)Cl.[O:6]1[C:10]2C=[CH:12][CH:13]=[CH:14][C:9]=2[CH2:8][CH2:7]1>C(Cl)Cl.CCOCC>[O:2]1[C:3]2[CH:7]=[CH:8][C:9]([CH:10]=[O:6])=[CH:14][C:13]=2[CH2:12][CH2:1]1

Participants

5

Reactant 2

HCID 10329DihydrobenzofuranHCID 21004Methane, dichloromethoxy-

Product 1

HCID 7359012,3-Dihydrobenzofuran-5-carboxaldehydeYield 60.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred solution of α,α-dichloromethyl methyl ether (2.15 g, 19 mmol, 1.35 eq) in methylene chloride (30 mL) at -40° C. was added successively stannic chloride (1.65 g, 17 mmol, 1.2 eq) and 15 minutes later, a solution of 2,3-dihydrobenzofuran (1.68 g, 14 mmol) in CH2Cl2 (5 mL) maintaining the temperature at or below -35° C. The mixture was warmed to 0° C., stirred 1 hour, then poured into ice-water, and stirred a further 30 minutes. The mixture was diluted with ether, and the phases separated. The organic phase was concentrated in vacuo, and the residue purified by vacuum distillation to yield the title compound (1.25 g, 60%) as a colorless liquid. b.p. 119-121° C. at 0.3 mm Hg.

Workup

  1. stirringstirred a further 30 minutes
  2. customthe phases separated
  3. concentrationThe organic phase was concentrated in vacuo
  4. distillationthe residue purified by vacuum distillation

Sources & evidence

ORD record
ord-d5b606d6e6474b53a5f8f579fd132168
Source dataset
uspto-grants-2000_12
Patent number
US06162927

Reaction notes

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