Hydrochloric Acid → 5-Hydroxy-1-indanone

HRID 278438Notes

Reaction equation

HRID 278438 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6]2.[Na].C(C1C=CC(S)=C(C)C=1)(C)(C)C.O.Cl>CCOC(C)=O>[OH:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 787875-Methoxyindan-1-oneHCID 70046092HCID 70046092, compound

Product 1

HCID 2331475-Hydroxy-1-indanoneYield 45.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

5-Methoxy-indan-1-one (8 g, 49.3 mmol), and 4-tert-butyl-2-methyl-benzenethiol sodium salt (11.92 g, 59.2 mmol) were heated at 142° C. for 1 hr under argon. After cooling to RT, water (80 ml) was added followed by 1N HCl (80 ml) and EtOAc (120 ml). The mixture was shaken and the aqueous phase extracted with EtOAc (100 ml), the combined organic extracts were washed with satd.NaCl solution (100 ml) and dried with Na2SO4, filtered and evaporated. The residue was chomatographed over SiO2 (Merck 230-400 mesh) eluting with EtOAc-nHexane (2:3), producing 5-hydroxy-indan-1-one (3.55g, 22.6 mmol, 45.9 %) as orange crystals Mp. 185-187° C., MS m/e=148.2 (M+).

Workup

  1. extractionthe aqueous phase extracted with EtOAc (100 ml)
  2. washthe combined organic extracts were washed with satd
  3. dry with materialNaCl solution (100 ml) and dried with Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. washeluting with EtOAc-nHexane (2:3)

Sources & evidence

ORD record
ord-6694c687bad94b2e8ec41dc5c8f13258
Source dataset
uspto-grants-2002_03
Patent number
US06359138B1

Reaction notes

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