Oxalyl chloride → HCID 59627906, compound

HRID 2088393Notes

Reaction equation

HRID 2088393 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 7 (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 8 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), 2.88 (t, J=7.8 Hz, 2H), 2.02 (t, J=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 173.9, 145.1, 110.7, 46.7, 37.3, 26.4, 24.8, 22.4.

Workup

  1. customA drying tube was placed on the flask
  2. concentrationwas concentrated in vacuo
  3. customThe crude acid chloride 8 was used in the next step without further purification

Sources & evidence

ORD record
ord-05185aaae8d74a2993e45ceffdbfdfb3
Source dataset
uspto-grants-2013_05
Patent number
US08435983B2

Reaction notes

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