3,5-Dimethyl-4-hydroxybenzaldehyde → HCID 59248991, compound

HRID 552288Notes

Reaction equation

HRID 552288 reaction equation
[CH2:1]([C:3]1[S:7][C:6]([C:8](=[O:10])[CH3:9])=[CH:5][C:4]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH3:17])[CH3:2].[CH3:18][C:19]1[CH:20]=[C:21]([CH:24]=[C:25]([CH3:28])[C:26]=1[OH:27])[CH:22]=O>C(O)C.Cl.C(O)(C)C.O>[CH2:1]([C:3]1[S:7][C:6]([C:8](=[O:10])[CH2:9][CH2:22][C:21]2[CH:24]=[C:25]([CH3:28])[C:26]([OH:27])=[C:19]([CH3:18])[CH:20]=2)=[CH:5][C:4]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH3:17])[CH3:2]

Participants

7

Reactant 2

HCID 752223,5-Dimethyl-4-hydroxybenzaldehydeHCID 67164648HCID 67164648, compound

Product 1

HCID 59248991HCID 59248991, compoundYield 27.6%

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

A solution of 1-(5-ethyl-4-o-tolyl-thiophen-2-yl)-ethanone (51 mg, 0.209 mmol) and 3,5-dimethyl-4-hydroxybenzaldehyde (47 mg, 0.172 mmol) in ethanol (1.5 mL) and 5 N HCl in isopropanol (0.7 mL) is stirred at it for 18 h. The solution is diluted with water and extracted with EA. The organic extract is evaporated, dissolved in methanol (3 mL) and THF (3 mL) and treated with Pd/C (10 mg, 10% Pd). The slurry is stirred under 1.5 bar of H2 for 18 h. The mixture is filtered, the solvent of the filtrate is removed in vacuo and the crude product is purified on prep. TLC plates with heptane:EA 3:1 to give 1-(5-ethyl-4-o-tolyl-thiophen-2-yl)-3-(4-hydroxy-3,5-dimethyl-phenyl)-propan-1-one (18 mg) as a colourless oil; LC-MS: tR=1.12 min, [M+1]+=379.24.

Workup

  1. extractionextracted with EA
  2. extractionThe organic extract
  3. customis evaporated
  4. dissolutiondissolved in methanol (3 mL)
  5. additionTHF (3 mL) and treated with Pd/C (10 mg, 10% Pd)
  6. filtrationThe mixture is filtered
  7. customthe solvent of the filtrate is removed in vacuo
  8. customthe crude product is purified on prep

Sources & evidence

ORD record
ord-a3a1e66e97c54b58b1cb3b3a0d27a9a0
Source dataset
uspto-grants-2011_05
Patent number
US07951794B2

Reaction notes

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