Acetic Acid → 2',4'-Dihydroxy-3'-propylacetophenone

HRID 868029Notes

Reaction equation

HRID 868029 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9]C)[C:4]=1[CH2:11][CH2:12][CH3:13].[C:14](O)(=[O:16])[CH3:15].Br>O>[CH2:11]([C:4]1[C:5]([OH:9])=[C:6]([C:14](=[O:16])[CH3:15])[CH:7]=[CH:8][C:3]=1[OH:2])[CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 5248571,3-Dimethoxy-2-propylbenzene

Product 1

HCID 27751982',4'-Dihydroxy-3'-propylacetophenone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1,3-Dimethoxy-2-propylbenzene (0.90 g, 5.0 mmol), glacial acetic acid (150 ml), and 48% aqueous hydrobromic acid (15 ml, 133 mmol) were combined and stirred at reflux temperature for three days. The mixture was allowed to cool to room temperature; poured into water (500 ml), and the aqueous solution extracted with ether (500 ml, 2×). The ether layers were combined, washed with brine, dried over magnesium sulfate, filtered and taken to dryness in vacuo. Flash chromatography as in Example 10 (plus an additional step of 5% ethyl acetate in hexane) yielded the title product: n.m.r.: δ12.97 (s, 1H), 7.52 (d, 1H), 6.38 (d, 1H), 5.79 (s, 1H), 2.63 (t, 2H), 2.56 (s, 3H), 1.58 (m, 2H), 0.98 (t, 3H).

Workup

  1. temperatureat reflux temperature for three days
  2. extractionthe aqueous solution extracted with ether (500 ml, 2×)
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered

Sources & evidence

ORD record
ord-2d297c9ec60b4e1dbb0221041fa430fc
Source dataset
uspto-grants-1988_10
Patent number
US04777299

Reaction notes

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