Thionyl Chloride → 2-Chromanecarbonyl chloride

HRID 1252677Notes

Reaction equation

HRID 1252677 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[CH2:4][CH2:3][CH:2]1[C:11]([OH:13])=O.S(Cl)([Cl:16])=O>>[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[CH2:4][CH2:3][CH:2]1[C:11]([Cl:16])=[O:13]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 27236653,4-dihydro-2H-1-benzopyran-2-carboxylic acid

Product 1

HCID 27945832-Chromanecarbonyl chloride

Procedure

A solution of 3,4-dihydro-1-benzopyran-2-carboxylic acid (0.59 g 3.3 mmol) in thionyl chloride (15 ml) was stirred at 20° C. for 16 hours. Excess thionyl chloride was evaporated, azeotroping with dry toluene, to give 3,4-dihydro-1-benzopyran-2-carboxylic acid chloride as a yellow oil (νmax (film) 1805 cm-1) which was used immediately.

Workup

  1. customExcess thionyl chloride was evaporated
  2. customazeotroping with dry toluene

Sources & evidence

ORD record
ord-73c2bee6628f480898c24ec8e6cef8d4
Source dataset
uspto-grants-1988_05
Patent number
US04745114

Reaction notes

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