Tetrahydrofuran → 4-Formylbenzoyl chloride

HRID 560971Notes

Reaction equation

HRID 560971 reaction equation
[C:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1)(O)=[O:2].O1CCCC1.C(Cl)(=O)C([Cl:20])=O>>[CH:8]([C:7]1[CH:10]=[CH:11][C:4]([C:1]([Cl:20])=[O:2])=[CH:5][CH:6]=1)=[O:9]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 120884-Formylbenzoic acidHCID 65578Oxalyl chloride

Product 1

HCID 124246204-Formylbenzoyl chloride

Conditions

Temperature
2.5 °C

Procedure

To a thin suspension of 4-carboxybenzaldehyde (600 g, 3.92 mol) in tetrahydrofuran (2664 g, 36.57 mol) was added dimethylformadehyde (11.48 g, 0.16 mol) and the reaction mixture was cooled to 0-5° C. with an ice bath. The reaction mixture was then stirred at 0° C. while oxalyl chloride (608.69 g, 4.70 mol) was added slowly. The reaction mixture was stirred until it was deemed complete by 1HNMR to yield the title compound. The reaction mixture was used in the next step without further manipulation.

Workup

  1. additionwas added dimethylformadehyde (11.48 g, 0.16 mol)
  2. additionwas added slowly

Sources & evidence

ORD record
ord-ff9d7ccf25914246a8288e265eabbb2d
Source dataset
uspto-grants-2011_11
Patent number
US08063206B2

Reaction notes

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