Sulfuric Acid → HCID 15525520, compound

HRID 381809Notes

Reaction equation

HRID 381809 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([OH:11])=[O:10].S(=O)(=O)(O)O.[CH:17](O)([CH3:19])[CH3:18]>>[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([O:11][CH:17]([CH3:19])[CH3:18])=[O:10]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 3776IsopropanolHCID 11970(2-Hydroxyphenyl)acetic acid

Product 1

HCID 15525520HCID 15525520, compound

Procedure

Isopropyl 2-hydroxyphenylacetate was prepared using the procedure described in J. Amer. Chem. Soc., 70, 1948, 1930. To a flask were added 10 g of 2-hydroxy phenylacetic acid, 99 mL of isopropanol and 9.9 mL of concentrated sulfuric acid. The mixture was refluxed for 5.5 hrs, poured into 400 mL of ice and extracted with 3×100 mL of ether. The organic layer was washed with 100 mL of aqueous solution of sodium bicarbonate (saturated). The organic fraction was dried over sodium sulfate and the solvent removed by rotary evaporation. The residue was flash chromatographed on silica gel eluted with 10% ethyl acetate/hexane to give 9.227 g of the desired product as a white solid. 1H NMR (300 Mhz, δ, CDCl3): 7.16 (m, 1H), 7.08 (dd, 1H), 6.92 (dd, 1H), 6.80 (m, 1H), 5.04 (septet, J=6.2 Hz, 1H), 3.60 (s, 2H), 1.25 (d, 6.2 Hz, 6H).

Workup

  1. temperatureThe mixture was refluxed for 5.5 hrs
  2. extractionextracted with 3×100 mL of ether
  3. washThe organic layer was washed with 100 mL of aqueous solution of sodium bicarbonate (saturated)
  4. dry with materialThe organic fraction was dried over sodium sulfate
  5. customthe solvent removed by rotary evaporation
  6. customchromatographed on silica gel
  7. washeluted with 10% ethyl acetate/hexane

Sources & evidence

ORD record
ord-e29354189ca0440bb24d12fddaf3b7be
Source dataset
uspto-grants-2001_10
Patent number
US06307107B1

Reaction notes

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