Hydrochloric Acid → methyl 2H-chromene-3-carboxylate

HRID 984118Notes

Reaction equation

HRID 984118 reaction equation
[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([C:11]([OH:13])=[O:12])[CH2:2]1.Cl.[CH3:15]O>>[CH3:15][O:12][C:11]([C:3]1[CH2:2][O:1][C:10]2[C:5]([CH:4]=1)=[CH:6][CH:7]=[CH:8][CH:9]=2)=[O:13]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3223042H-chromene-3-carboxylic acid

Product 1

HCID 1475903methyl 2H-chromene-3-carboxylate

Procedure

Compound 16B (5 g) and concentrated HCl (2 mL) in MeOH (200 mL) were heated to reflux for 30 h. The reaction mixture was quenched with water (200 mL) and ether (200 mL). Separated the organic layer, washed with water, brine, dried (MgSO4), concentrated to give an off-white solid, compound 16C (4.2 g). mp 56-57° C.; MS: 191 (M+1)+. Preparation of 6-Chlorosulfonyl-2H-chromene-3-carboxylic acid methyl ester (Compound 16D)

Workup

  1. temperatureto reflux for 30 h
  2. customThe reaction mixture was quenched with water (200 mL) and ether (200 mL)
  3. customSeparated the organic layer
  4. washwashed with water, brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-94b92336bbf5484aa225a0c81d090256
Source dataset
uspto-grants-2005_03
Patent number
US06867224B2

Reaction notes

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