Sulfuric Acid → HCID 12715505, compound

HRID 894387Notes

Reaction equation

HRID 894387 reaction equation
[C:1]1([CH:7]([CH:12]([C:14]([OH:16])=O)[CH3:13])[CH2:8][C:9]([OH:11])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(=O)(=O)(O)O>>[CH3:13][CH:12]1[CH:7]([CH2:8][C:9]([OH:11])=[O:10])[C:1]2[C:2](=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:14]1=[O:16]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 12881384HCID 12881384, compound

Product 1

HCID 12715505HCID 12715505, compoundYield 79.4%

Procedure

2-Phenylbutane-1,3-dicarboxylic acid (Swan, J. Chem. Soc., 1955, 1039) (20.0 g, 90.0 mmol) was dissolved in 300 ml. concentrated sulfuric acid and heated at 100° for 24 hr. The hot solution was poured onto 1 kg ice and the mixture extracted with 5×250 ml. ether. The ether phases were washed with brine, dried over magnesium sulfate, filtered, and vacuum evaporated to yield a pale yellow syrup 14.6 g. (79%), m/e 222. The NMR spectrum indicated the presence of only one major isomer as evidenced by a single upfieled doublet, assigned to the 2-methyl substituent, and small amounts of three other isomers.

Workup

  1. extractionthe mixture extracted with 5×250 ml
  2. washThe ether phases were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customvacuum evaporated

Sources & evidence

ORD record
ord-7f237d51eb734a0a8fdab18de0e48f29
Source dataset
uspto-grants-1981_08
Patent number
US04283539

Reaction notes

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