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

HRID 45459Notes

Reaction equation

HRID 45459 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 on an ice bath under nitrogen and 1M phenylmagnesium bromide in tetrahydrofuran (60 mL, 60 mmol, 1.2 equiv.) was added over 20 min. Stirring was continued for 3 hr at room temperature. The reaction mixture 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). The organic layer was dried over sodium sulfate, filtered and the solvent was removed on a rotary evaporator. Crude 24 (19.2 g, 105%) was used in the next step without purification.

Workup

  1. extractionextracted with ethyl acetate (800 mL)
  2. extractionThe organic extract
  3. washwas washed with water (2×400 mL)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. customthe solvent was removed on a rotary evaporator
  7. customCrude 24 (19.2 g, 105%) was used in the next step without purification

Sources & evidence

ORD record
ord-acbd4e631f4140feb356af88baa1030a
Source dataset
uspto-grants-2013_09
Patent number
US08541522B2

Reaction notes

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