Oxalyl chloride → HCID 59627906, compound

HRID 1367670Notes

Reaction equation

HRID 1367670 reaction equation
[CH3:1][C:2](=[CH2:10])[CH2:3][CH2:4][CH2:5][CH2:6][C:7](O)=[O:8].C(Cl)(=O)C([Cl:14])=O>C1C=CC=CC=1>[CH3:1][C:2](=[CH2:10])[CH2:3][CH2:4][CH2:5][CH2:6][C:7]([Cl:14])=[O:8]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 198539716-Methylhept-6-enoic acid

Product 1

HCID 59627906HCID 59627906, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of the carboxylic acid 71 (2.2 g, 15.5 mmol) in benzene (30 ml), was added oxalyl chloride (3 ml, 34.4 mmol, 2.22 equiv). A drying tube was placed on the flask and the reaction mixture was stirred for 90 min at room temperature before it was concentrated in vacuo. The crude acid chloride was used in the next step without further purification: TLC Rf=0.37 (silica gel, 25% EtOAc/hexanes); 1H NMR (600 MHz, CDCl3) δ 4.69 (s, 1H), 4.67 (s, 1H), 2.90-2.87 (t, 3J=7.8 Hz, 2H), 2.03-2.00 (t, 3J=7.8 Hz, 2H), 1.74-1.66 (m, 2H), 1.69 (s, 3H), 1.58-1.46 (m, 2H); 13C NMR (100 MHz, CDCl3) δ 173.979, 145.086, 110.717, 46.663, 37.334, 26.421, 24.799, 22.431.

Workup

  1. customA drying tube was placed on the flask
  2. concentrationwas concentrated in vacuo
  3. customThe crude acid chloride was used in the next step without further purification

Sources & evidence

ORD record
ord-66e15831dc7b496d8ff6901b4fa8ffb5
Source dataset
uspto-grants-2011_02
Patent number
US07893268B2

Reaction notes

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