Oxalyl chloride → 5-(Benzyloxy)pentanoyl chloride

HRID 1367665Notes

Reaction equation

HRID 1367665 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C([Cl:19])=O>C1C=CC=CC=1>[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([Cl:19])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 104205755-(Benzyloxy)pentanoic acid

Product 1

HCID 102631205-(Benzyloxy)pentanoyl chloride

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of the acid 29 (4.98 g, 24 mmol) in dry benzene (40 ml), was added oxalyl chloride (2.5 ml, 28.8 mmol, 1.2 equiv) dropwise. A drying tube was placed on the flask and the reaction was stirred for 90 min at room temperature. The reaction was concentrated in vacuo and used directly in the next step: 1H NMR (400 MHz, CDCl3) δ 7.38-7.27 (m, 5H), 4.50 (s, 2H), 3.51-3.40 (t, 3J=6.4 Hz, 2H), 2.95-2.90 (t, 3J=7.2 Hz, 3H), 1.87-1.78 (m, 2H), 1.71-1.63 (m, 2H); 13C NMR (75 MHz, CDCl3) δ 173.958, 138.519, 128.949, 128.787, 128.630, 127.862, 73.197, 69.551, 47.032, 28.618, 22.329.

Workup

  1. customA drying tube was placed on the flask
  2. concentrationThe reaction was concentrated in vacuo

Sources & evidence

ORD record
ord-1d18e44234d34735bf07cd7d56a45342
Source dataset
uspto-grants-2011_02
Patent number
US07893268B2

Reaction notes

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