Water → HCID 21504752, compound

HRID 1288329Notes

Reaction equation

HRID 1288329 reaction equation
[C:1]([C:4]1[O:5][C:6]2[C:14]([Cl:15])=[CH:13][C:12]3[C:16]4[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=4[CH2:18][O:19][C:11]=3[C:7]=2[C:8](=[O:10])[CH:9]=1)([OH:3])=[O:2].O.[S:25](=[O:29])(=O)([OH:27])[OH:26]>>[CH2:1]([O:2][C:1]([C:4]1[O:5][C:6]2[C:14]([Cl:15])=[CH:13][C:12]3[C:16]4[CH:23]=[CH:22][C:21]([S:25]([OH:27])(=[O:29])=[O:26])=[CH:20][C:17]=4[CH2:18][O:19][C:11]=3[C:7]=2[C:8](=[O:10])[CH:9]=1)=[O:3])[CH2:4][CH2:9][CH3:8]

Participants

4

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 21504764HCID 21504764, compound

Product 1

HCID 21504752HCID 21504752, compound

Procedure

A solution of 7.0 gm (0.022 mol) of 2-chloro-6H-dibenzo-[b,d]-pyranyl-(3)-fumaric acid ether in concentrated sulfuric acid (see Example 9) was stirred for 2 hours at room temperature. The dark reaction mixture was then poured into ice water, and the resulting precipitate, consisting mainly of 2-carboxy-4-oxo-12-chloro-4H,6H-[2]-benzopyrano-[3,4-f][1]-benzopyran, was filtered off. The aqueous phase was extracted with n-butanol, and the obtained solution was evaporated to dryness. After addition of ether, 2.5 gm (23.8% of theory) of the compound named in the heading, m.p. 95°-97° C, were obtained (contained 3 mols of water of crystallization).

Workup

  1. customThe dark reaction mixture
  2. filtrationwas filtered off
  3. extractionThe aqueous phase was extracted with n-butanol
  4. customthe obtained solution was evaporated to dryness
  5. additionAfter addition of ether, 2.5 gm (23.8% of theory) of the compound
  6. customwere obtained

Sources & evidence

ORD record
ord-d0c6026d7b4b41568d3728a7b510defc
Source dataset
uspto-grants-1976_10
Patent number
US03987186

Reaction notes

Loading…