Ammonium Chloride → (2-(Benzyloxy)biphenyl-3-yl)(phenyl)methanol

HRID 1042513Notes

Reaction equation

HRID 1042513 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([CH:15]=[O:16])=[CH:13][CH:12]=[CH:11][C:10]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23]1([Mg]Br)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[Cl-].[NH4+]>O1CCCC1>[CH2:1]([O:8][C:9]1[C:14]([CH:15]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[OH:16])=[CH:13][CH:12]=[CH:11][C:10]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 218409602-(Benzyloxy)-[1,1'-biphenyl]-3-carbaldehydeHCID 178418255HCID 178418255, compound

Product 1

HCID 58238513(2-(Benzyloxy)biphenyl-3-yl)(phenyl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-(benzyloxy)biphenyl-3-carbaldehyde (14.4 g, 50 mmol) in anhydrous tetrahydrofuran (180 mL) was stirred under nitrogen on an ice bath and 1M phenyl magnesium bromide in tetrahydrofuran (60 mL, 60 mmol) was added over 20 min. The reaction mixture was stirred at room temperature for 3 hr, after which it was poured on saturated ammonium chloride (600 mL) and extracted with ethyl acetate (800 mL). The organic extract was washed with water (2×400 mL), dried over sodium sulfate and stripped. The crude product (19.2 g) was used as such in the next step.

Workup

  1. extractionextracted with ethyl acetate (800 mL)
  2. extractionThe organic extract
  3. washwas washed with water (2×400 mL)
  4. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-50bde2a3b68545a7bfda15702ff73843
Source dataset
uspto-grants-2013_10
Patent number
US08557936B2

Reaction notes

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