Coumarin-3-Carboxylic Acid → Coumarin-3-carbonyl chloride

HRID 1719190Notes

Reaction equation

HRID 1719190 reaction equation
[O:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([C:12]([OH:14])=O)[C:2]1=[O:3].S(Cl)([Cl:17])=O>ClCCl>[O:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([C:12]([Cl:17])=[O:14])[C:2]1=[O:3]

Participants

4

Reactant 2

HCID 10752Coumarin-3-Carboxylic AcidHCID 24386Thionyl Chloride

Product 1

HCID 11572010Coumarin-3-carbonyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Coumarin-3-carboxylic acid (2.1 g, 10 m mole) was suspended in dry dichloromethane (10 ml) and heated at reflux for 2 h with thionyl chloride (5 ml). After this time a small amount of insoluble material was filtered off and petroleum ether 60°-80° C. (35 ml) was added to the filtrate. The acid chloride was filtered, washed with ether and dried (1.63 g, 71%), mp 138°-41° C.; νmax (CHCl3) 1790, 1740, 1610, 1570 cm-1 ; δ (CDCl3) 7.30-8.10 (4H, m, phenyls), 8.95 (1H, s, coumarin 4-H).

Workup

  1. temperatureheated
  2. filtrationAfter this time a small amount of insoluble material was filtered off
  3. additionpetroleum ether 60°-80° C. (35 ml) was added to the filtrate
  4. filtrationThe acid chloride was filtered
  5. washwashed with ether
  6. customdried (1.63 g, 71%), mp 138°-41° C.

Sources & evidence

ORD record
ord-024b0b83ad2a4200b7989ecc8b52ce01
Source dataset
uspto-grants-1985_09
Patent number
US04539149

Reaction notes

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