(2-Butylbenzofuran-3-yl) (4-hydroxyphenyl) ketone → 4-[(2-Butyl-benzofuran-3-yl)-hydroxy-methyl]-phenol

HRID 1067376Notes

Reaction equation

HRID 1067376 reaction equation
[CH2:1]([C:5]1[O:6][C:7]2[CH:22]=[CH:21][CH:20]=[CH:19][C:8]=2[C:9]=1[C:10](=[O:18])[C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)[CH2:2][CH2:3][CH3:4].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH2:1]([C:5]1[O:6][C:7]2[CH:22]=[CH:21][CH:20]=[CH:19][C:8]=2[C:9]=1[CH:10]([OH:18])[C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 96670(2-Butylbenzofuran-3-yl) (4-hydroxyphenyl) ketoneHCID 21226445Aluminium lithium hydride

Product 1

HCID 234456214-[(2-Butyl-benzofuran-3-yl)-hydroxy-methyl]-phenol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-10 °C

Procedure

A solution containing commercial 2-n-butyl-3-(4-hydroxybenzoyl)benzofuran (0.500 g, 17.0 mmol) and lithium aluminum hydride (34.0 mmol) in THF (84 mL) was refluxed for 3 h. The reaction was cooled to −10° C., and carefully quenched with 0.1N NaOH and H2O. The aqueous solution was extracted with ether and concentrated. Purification on silica gel gave the title compound as a white solid, mp 94-96° C. (DMSO-d6) δ0.90 (t, 3H), 1.35 (sextet, 2H), 1.64 (quintet, 2H), 2.84 (t, 2H), 5.67 (d, 1H), 5.87 (d, 1H), 6.69 (d, 2H), 7.07 (t, 1H), 7.15 (dt, 1H), 7.22 (d, 2H), 7.40-7.43 (m, 2H), 9.24 (s, 1H). IR (KBr) 3350, 2950, 1610, 1510 and 1450 cm−1. mass spectrum (EI) m/z 296 (M+). Anal. Calcd. for C19H20O3: C, 77.00; H, 6.80; N, 0.00. Found: C, 75.63; H, 6.86; N, 0.04.

Workup

  1. temperaturewas refluxed for 3 h
  2. customcarefully quenched with 0.1N NaOH and H2O
  3. extractionThe aqueous solution was extracted with ether
  4. concentrationconcentrated
  5. customPurification on silica gel

Sources & evidence

ORD record
ord-3b9a3784b62344fba1d8ae15a79338a8
Source dataset
uspto-grants-2001_06
Patent number
US06248764B1

Reaction notes

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