3,5-Dimethyl-4-hydroxybenzaldehyde → HCID 59248994, compound

HRID 552272Notes

Reaction equation

HRID 552272 reaction equation
[CH3:1][C:2]1[S:6][C:5]([C:7](=[O:9])[CH3:8])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[CH3:16][C:17]1[CH:18]=[C:19]([CH:22]=[C:23]([CH3:26])[C:24]=1[OH:25])[CH:20]=O>C(O)C.Cl.C(O)(C)C.O>[OH:25][C:24]1[C:23]([CH3:26])=[CH:22][C:19]([CH2:20][CH2:8][C:7]([C:5]2[S:6][C:2]([CH3:1])=[C:3]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH:4]=2)=[O:9])=[CH:18][C:17]=1[CH3:16]

Participants

7

Reactant 2

HCID 752223,5-Dimethyl-4-hydroxybenzaldehydeHCID 818940Ethanone, 1-(5-methyl-4-phenyl-2-thienyl)-

Product 1

HCID 59248994HCID 59248994, compoundYield 52.9%

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

A solution of 1-(5-methyl-4-phenyl-thiophen-2-yl)-ethanone (419 mg, 1.94 mmol) and 3,5-dimethyl-4-hydroxybenzaldehyde (350 mg, 2.33 mmol) in ethanol (4 mL) and 5 N HCl in isopropanol (2 mL) is stirred at it for 1 h. The dark green solution is diluted with water and extracted with EA. The organic extract is evaporated, dissolved in ethanol (10 mL) and treated with Pd/C (60 mg, 10% Pd). The slurry is hydrogenated under 1.4 bar of H2 for 6 h. The mixture is filtered, the solvent is removed in vacuo and the crude product is purified by CC on silica gel eluting with heptane:EA 4:1 to give 3-(4-hydroxy-3,5-dimethyl-phenyl)-1-(5-methyl-4-phenyl-thiopen-2-yl)-propan-1-one (360 mg) as a colourless resin; LC-MS: tR=1.09 min, [M+1]+=351.25; 1H NMR (CDCl3): δ 7.60 (s, 1H), 7.46-7.30 (m, 5H), 6.85 8s, 2H), 4.48 (s, 1H), 3.14 (dd, J=7.0, 8.2 Hz, 2H), 2.92 (dd, J=7.0, 8.2 Hz, 2H), 2.52 (s, 3H), 2.21 (s, 6H).

Workup

  1. extractionextracted with EA
  2. extractionThe organic extract
  3. customis evaporated
  4. dissolutiondissolved in ethanol (10 mL)
  5. additiontreated with Pd/C (60 mg, 10% Pd)
  6. filtrationThe mixture is filtered
  7. customthe solvent is removed in vacuo
  8. customthe crude product is purified by CC on silica gel eluting with heptane:EA 4:1

Sources & evidence

ORD record
ord-e5a3de529f8546c49b2db16bd081d995
Source dataset
uspto-grants-2011_05
Patent number
US07951794B2

Reaction notes

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