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

HRID 1245150Notes

Reaction equation

HRID 1245150 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Mg].[CH3:17][O:18][C:19]1[C:20]([CH3:33])=[C:21]([C:24]([O:31][CH3:32])=[C:25]([O:29][CH3:30])[C:26]=1[O:27][CH3:28])[CH:22]=[O:23].[Cl-].[NH4+]>O1CCCC1>[CH3:17][O:18][C:19]1[C:20]([CH3:33])=[C:21]([CH:22]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[OH:23])[C:24]([O:31][CH3:32])=[C:25]([O:29][CH3:30])[C:26]=1[O:27][CH3:28]

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 8028TetrahydrofuranSolvent2×

Procedure

Under ice-cooling, into a Grignard reagent (35 ml, a tetrahydrofuran solution) prepared from 2-(benzyloxy)bromobenzene (11.50 g, 0.044 mol) and magnesium (1.16 g, 0.048 mol) was dropped a solution of 3,4,5,6-tetramethoxy-2-methylbenzaldehyde (5.00 g, 0.021 mol) in anhydrous tetrahydrofuran (30 ml) and the mixture was stirred for 2 hours more. The reaction solution was poured into a saturated aqueous solution of ammonium chloride followed by extracting with ether. The extract was washed with a saturated saline and dried. The reaction solution was filtered and the crude product obtained by concentrating the filtrate was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to give the title compound (8.80 g, 0.021 mol, 99%).

Workup

  1. extractionby extracting with ether
  2. washThe extract was washed with a saturated saline
  3. customdried
  4. filtrationThe reaction solution was filtered
  5. customthe crude product obtained
  6. concentrationby concentrating the filtrate
  7. customwas purified by silica gel column chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-b5b4ae8034ba4a33955741293ecd4b10
Source dataset
uspto-grants-2006_10
Patent number
US07122543B2

Reaction notes

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