Thionyl Chloride → 6-(Chlorocarbonyl)naphthalen-2-yl acetate

HRID 492269Notes

Reaction equation

[C:1]([O:4][C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:15]([OH:17])=O)[CH:11]=2)[CH:6]=1)(=[O:3])[CH3:2].S(Cl)([Cl:20])=O>CN(C)C=O.O1CCCC1>[C:1]([O:4][C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:15]([Cl:20])=[O:17])[CH:11]=2)[CH:6]=1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

1 g (0.1 mole) of 2-acetoxy-6-naphthoic acid, 0.1 g of N,N-dimethylformamide and 185 g of tetrahydrofuran were fed into. 300 ml-glass container. To this mixture, 23.9 g of thionyl chloride was added dropwise at room temperature under stirring. Then, the reaction was heated to 50° C. and kept at this temperature for 30 minutes. From the resulting mixture, tetrahydrofuran and the excess thionyl chloride were distilled out using a rotary evaporator to give 24.9 g (0.1 mole) of 2-acetoxy-6-naphthoic acid chloride.

Workup

distillationFrom the resulting mixture, tetrahydrofuran and the excess thionyl chloride were distilled out
customa rotary evaporator

Sources & evidence

ORD record: ord-3edf50f6bc924ca6bb59fa5fc035d649
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07531691B2

Reaction notes

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