Hydrochloric Acid → 2-(1-Oxo-1,3-dihydroisobenzofuran-5-yl)acetaldehyde

HRID 1848401Notes

Reaction equation

HRID 1848401 reaction equation
[O:1]1CCO[CH:2]1[CH2:6][C:7]1[CH:16]=[CH:15][C:10]2[C:11](=[O:14])[O:12][CH2:13][C:9]=2[CH:8]=1.Cl>O>[O:14]=[C:11]1[C:10]2[CH:15]=[CH:16][C:7]([CH2:6][CH:2]=[O:1])=[CH:8][C:9]=2[CH2:13][O:12]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 585863105-[1,3]dioxolan-2-ylmethyl-3H-isobenzofuran-1-one

Product 1

HCID 772312612-(1-Oxo-1,3-dihydroisobenzofuran-5-yl)acetaldehyde

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

5-(1,3-Dioxolan-2-ylmethyl)-2-benzofuran-1(3H)-one (61 g, 280 mmol) was combined with water (2.2 L) in a 5 L round bottomed flask equipped with a Claisen adapter, thermocouple, stir bar and nitrogen bubbler. Aqueous HCl solution (2M, 1.14 L, 2.29 mol) was added and the resulting mixture was heated at 40° C. for 8 h. Then the mixture was stirred overnight at room temperature. The mixture was extracted three times with 2 L of ethyl acetate. The combined organic layers were concentrated to give (1-oxo-1,3-dihydro-2-benzofuran-5-yl)acetaldehyde. LC-MS (IE, m/z): 177 (M+1)+.

Workup

  1. customequipped with a Claisen adapter
  2. stirringThen the mixture was stirred overnight at room temperature
  3. extractionThe mixture was extracted three times with 2 L of ethyl acetate
  4. concentrationThe combined organic layers were concentrated

Sources & evidence

ORD record
ord-a1f0b296d844470cb05a226776523d67
Source dataset
uspto-grants-2015_02
Patent number
US08952166B2

Reaction notes

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