Thionyl Chloride → 2-Chromanecarbonyl chloride

HRID 1081306

Reaction equation

[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH:2]1[C:11]([OH:13])=O.S(Cl)([Cl:16])=O>>[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH:2]1[C:11]([Cl:16])=[O:13]

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 27236653,4-dihydro-2H-1-benzopyran-2-carboxylic acid

Product 1

HCID 27945832-Chromanecarbonyl chlorideYield 98%

Procedure

89.0 g (0.5 mol) chroman-2-carboxylic acid and 71.4 g (0.6 mol) thionyl chloride were heated to 80° for 4-5 hours (end of gas evolution). Destillation (77°-80°/0.1 torr) yielded 96.0 g (98%) chroman-2-carboxylic acid chloride

Sources & evidence

ORD record: ord-48084b6daa9143d7ab9d40018a8d363c
Source dataset: uspto-grants-1996_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05585392

Linked notes

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