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

HRID 1830211Notes

Reaction equation

HRID 1830211 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:31]=[CH:30][CH:29]=[CH:28][C:27]=1Br)[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:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2[O:25][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=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 5618281-(Benzyloxy)-2-bromobenzeneHCID 5462224MagnesiumHCID 148523342,3,4,5-Tetramethoxy-6-methylbenzaldehyde

Product 1

HCID 219191851-(3,4,5,6-Tetramethoxy-2-methylphenyl)-1-(2-benzyloxyphenyl)methanolYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

An anhydrous tetrahydrofuran (30 ml) solution of 3,4,5,6-tetramethoxy-2-methylbenzaldehyde (5.00 g, 0.021 mol) was added dropwise under ice cooling to a Grignard reagent (35 ml tetrahydrofuran solution) prepared from 2-(benzyloxy)bromobenzene (11.50 g, 0.044 mol) and magnesium (1.16 g, 0.048 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 (8.80 g, 0.021 mol, 99%).

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-3e54cfd0d431419a84275ea75627c759
Source dataset
uspto-grants-2006_06
Patent number
US07064124B2

Reaction notes

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