(2-(Benzyloxy)-3-tert-butylphenyl)(2'-methoxybiphenyl-3-yl)(phenyl)methanol → 2-tert-Butyl-6-((2'-methoxybiphenyl-3-yl)(phenyl)methyl)phenol

HRID 45467Notes

Reaction equation

HRID 45467 reaction equation
C([O:8][C:9]1[C:14]([C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:13][CH:12]=[CH:11][C:10]=1[C:19]([C:27]1[CH:28]=[C:29]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=2[O:39][CH3:40])[CH:30]=[CH:31][CH:32]=1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)O)C1C=CC=CC=1>C(#N)C.[PH2](O)=O>[C:15]([C:14]1[CH:13]=[CH:12][CH:11]=[C:10]([CH:19]([C:27]2[CH:28]=[C:29]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=3[O:39][CH3:40])[CH:30]=[CH:31][CH:32]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:9]=1[OH:8])([CH3:18])([CH3:16])[CH3:17]

Participants

4

Reactant 1

HCID 58238592(2-(Benzyloxy)-3-tert-butylphenyl)(2'-methoxybiphenyl-3-yl)(phenyl)methanol

Product 1

HCID 582385792-tert-Butyl-6-((2'-methoxybiphenyl-3-yl)(phenyl)methyl)phenolYield 96%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 4124402Phosphinic AcidSolvent

Procedure

A solution of 29 (1.2 g, 2.27 mmol) in acetonitrile (70 mL) and 50% aqueous hypophosphorous acid (30 mL) was kept at reflux for 3.5 hr. The acetonitrile was removed in vacuo, the residue was diluted with ethyl acetate (150 mL) and water (100 mL). Phases were separated. The organic phase was washed with saturated sodium bicarbonate (2×100 mL) and water (100 mL), dried over sodium sulfate and filtered. The solvent was removed on a rotary evaporator. The crude product was purified by chromatography on silica (45 g) with hexane (2 L) to yield pure D4 (0.92 g, 96%).

Workup

  1. temperatureat reflux for 3.5 hr
  2. customThe acetonitrile was removed in vacuo
  3. additionthe residue was diluted with ethyl acetate (150 mL) and water (100 mL)
  4. customPhases were separated
  5. washThe organic phase was washed with saturated sodium bicarbonate (2×100 mL) and water (100 mL)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customThe solvent was removed on a rotary evaporator
  9. customThe crude product was purified by chromatography on silica (45 g) with hexane (2 L)

Sources & evidence

ORD record
ord-5329472e5a74487e9b3adca193aef5b7
Source dataset
uspto-grants-2013_09
Patent number
US08541522B2

Reaction notes

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