Hydrochloric Acid → HCID 11839188, compound

HRID 1890143Notes

Reaction equation

HRID 1890143 reaction equation
[C:1]1([S:7][CH:8]2[CH2:12][C:11](=[O:13])[O:10][C:9]2=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl-].[Al+3].[Cl-].[Cl-].Cl>C(Cl)Cl>[O:13]=[C:11]1[C:6]2[C:1](=[CH:2][CH:3]=[CH:4][CH:5]=2)[S:7][CH:8]([C:9]([OH:10])=[O:14])[CH2:12]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6451240Aluminum(III) ChlorideHCID 13075159HCID 13075159, compound

Product 1

HCID 11839188HCID 11839188, compoundYield 47.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Crude 3-phenylsulfanyl-dihydro-furan-2,5-dione (20 g, 91 mmol) was dissolved in CH2Cl2 (30 ml) and cooled to 0° C. Aluminum chloride (18.16 g, 136 mmol) was added and the mixture was stirred at room temperature for 1.5 hr. The reaction mixture was diluted with CH2Cl2 (1000 ml) and poured into ice-cooled conc HCl (1000 ml). The phases were separated and the aqueous phase was extracted with CH2Cl2(×3). The combined organic phases were washed with water, dried (MgSO4) and evaporated to a brown solid. The solid was triturated with Et2O to give 8.98 g of 4-oxo-thiochroman-2-carboxylic acid as a pale brown solid. 1H NMR (DMSO) δ 7.96 (1H, dd), 7.20-7.60 (3H, m), 4.40 (1H, dd), 3.20-3.33 (2H, m).

Workup

  1. additionpoured into ice-
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted with CH2Cl2(×3)
  4. washThe combined organic phases were washed with water
  5. dry with materialdried (MgSO4)
  6. customevaporated to a brown solid
  7. customThe solid was triturated with Et2O

Sources & evidence

ORD record
ord-ea2f208fd0f9497991a1b481a9649512
Source dataset
uspto-grants-2013_08
Patent number
US08506932B2

Reaction notes

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