Ammonium Chloride → 1-(3,4,5,6-Tetramethoxy-2-methylphenyl)-1-(3-benzyloxyphenyl)methanol

HRID 1830209Notes

Reaction equation

HRID 1830209 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH3:17])=[C:5]([C:8]([O:15][CH3:16])=[C:9]([O:13][CH3:14])[C:10]=1[O:11][CH3:12])[CH:6]=[O:7].[CH2:18]([O:25][C:26]1[CH:27]=[C:28](Br)[CH:29]=[CH:30][CH:31]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[Mg].[Cl-].[NH4+]>O1CCCC1>[CH3:1][O:2][C:3]1[C:4]([CH3:17])=[C:5]([CH:6]([C:28]2[CH:29]=[CH:30][CH:31]=[C:26]([O:25][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:27]=2)[OH:7])[C:8]([O:15][CH3:16])=[C:9]([O:13][CH3:14])[C:10]=1[O:11][CH3:12]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 27566381-(Benzyloxy)-3-bromobenzeneHCID 5462224MagnesiumHCID 148523342,3,4,5-Tetramethoxy-6-methylbenzaldehyde

Product 1

HCID 220541901-(3,4,5,6-Tetramethoxy-2-methylphenyl)-1-(3-benzyloxyphenyl)methanolYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

An anhydrous tetrahydrofuran (50 ml) solution of 3,4,5,6-tetramethoxy-2-methylbenzaldehyde (14 g, 0.058 mol) was added dropwise under ice cooling to a Grignard reagent (150 ml tetrahydrofuran solution) prepared from 3-(benzyloxy)bromobenzene (18.4 g, 0.070 mol) and magnesium (1.87 g, 0.077 mol), and the resulting solution was stirred for 2 hours. The reaction solution was poured in an aqueous solution of saturated ammonium chloride and extracted with ether. The extract was washed with saturated brine and then dried. The reaction solution was filtered, the filtrate was concentrated and the obtained crude product was purified by silica gel column chromatography (hexand:ethyl acetate=4:1) to obtain the titled compound (23.5 g, 0.055 mol, 95%).

Workup

  1. extractionextracted with ether
  2. washThe extract was washed with saturated brine
  3. customdried
  4. filtrationThe reaction solution was filtered
  5. concentrationthe filtrate was concentrated
  6. customthe obtained crude product
  7. customwas purified by silica gel column chromatography (hexand:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-90161aa5746a4560a61d570802f2a027
Source dataset
uspto-grants-2006_06
Patent number
US07064124B2

Reaction notes

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