5-Methoxyindan-1-one → 5-Hydroxy-1-indanone

HRID 1742417Notes

Reaction equation

HRID 1742417 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>Br.CC(O)=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

3

Reactant 1

HCID 787875-Methoxyindan-1-one

Product 1

HCID 2331475-Hydroxy-1-indanoneYield 36%

Reagents, catalysts & solvents 1

HCID 21893785Acetic Acid Mixture with Hydrobromic AcidSolvent

Conditions

Temperature
23 °C

Procedure

A solution of 5-methoxy-indan-1-one (4.9 grams, 30 mmol)in 1:1 concentrated HBr/HOAc (150 mL) was heated at 112° C. for 28 hours. The reaction was cooled to 23° C. and filtered through celite. The filtrate was diluted with ethyl acetate (1000 mL) and washed with saturated aqueous NaCl (100 mL), saturated aqueous NaHCO3 (2×100 mL) and with saturated aqueous NaCl (100 mL). The ethyl acetate solution was dried (MgSO4) and concentrated in vacuo to give 1.6 grams of crude product. 1H NMR (250 MHz, d6 -DMSO): d 7.45 (d, 1 H), 6.82 (s, 1 H), 6.78 (d, 1 H), 2.95 (t, 2H), 2.55 (t, 2 H).

Workup

  1. filtrationfiltered through celite
  2. additionThe filtrate was diluted with ethyl acetate (1000 mL)
  3. washwashed with saturated aqueous NaCl (100 mL), saturated aqueous NaHCO3 (2×100 mL) and with saturated aqueous NaCl (100 mL)
  4. dry with materialThe ethyl acetate solution was dried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-457f4a3b54694e22a467f2b2e48a7351
Source dataset
uspto-grants-1994_08
Patent number
US05338740

Reaction notes

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