Thionyl Chloride → 2-Ethoxycarbonyloxy-5-octanoylbenzoyl chloride

HRID 1398277Notes

Reaction equation

[CH2:1]([O:3][C:4]([O:6][C:7]1[CH:15]=[CH:14][C:13]([C:16](=[O:24])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:12][C:8]=1[C:9](O)=[O:10])=[O:5])[CH3:2].S(Cl)([Cl:27])=O>C1(C)C=CC=CC=1.N1C=CC=CC=1>[CH2:1]([O:3][C:4]([O:6][C:7]1[CH:15]=[CH:14][C:13]([C:16](=[O:24])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:12][C:8]=1[C:9]([Cl:27])=[O:10])=[O:5])[CH3:2]

Participants

Conditions

Temperature: 55 °C

Procedure

5.59 g (16.6 mmol) of 2-ethoxycarbonyloxy-5-octanoylbenzoic acid are dissolved in 56 ml of toluene with a few drops of pyridine. 1.45 ml (20 mmol) of thionyl chloride are added dropwise and the mixture is stirred at 55° C. for 14 hours and then concentrated to dryness. 5.79 g of 2-ethoxycarbonyloxy-5-octanoylbenzoyl chloride are obtained in a yield of 98%.

Workup

concentrationconcentrated to dryness

Sources & evidence

ORD record: ord-77a08b6ecbfd45ac84b43d4a568e9397
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901357B2

Reaction notes

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