Benzyl Alcohol → (3'-Benzyloxybiphenyl-2-yl)methanol

HRID 278168Notes

Reaction equation

HRID 278168 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:15]2[CH:30]=[CH:29][CH:28]=[CH:27][C:16]=2[C:17](OCC2C=CC=CC=2)=[O:18])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].C(O)C1C=CC=CC=1>C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:15]2[CH:30]=[CH:29][CH:28]=[CH:27][C:16]=2[CH2:17][OH:18])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 21226445Aluminium lithium hydrideHCID 22627078Benzyl 2-(3'-benzyloxyphenyl)benzoate

Product 1

HCID 22627088(3'-Benzyloxybiphenyl-2-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of benzyl 2-(3′-benzyloxyphenyl)benzoate from Step D (1.35 g, 3.42 mmol) in dry THF (20+10 mL) was added dropwise to a stirred suspension of LiAlH4 (0.26 g, 6.84 mmol) in THF (30 mL) at 0° C., under argon. Stirring was continued for 1 hour at 0° C., then the reaction was quenched with wet ether, followed by water, then aq. NH4Cl. The resulting mixture was extracted with EtOAc (2×100 mL), and the combined organic extracts were dried over Na2SO4, filtered, and concentrated under reduced pressure to give a crude product which contained benzyl alcohol. Vacuum distillation (1 mm Hg, 80° C.) allowed removal of most of the benzyl alcohol to give the titled product as a pale solid.

Workup

  1. customthe reaction was quenched with wet ether
  2. extractionThe resulting mixture was extracted with EtOAc (2×100 mL)
  3. dry with materialthe combined organic extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto give a crude product which
  7. distillationVacuum distillation (1 mm Hg, 80° C.)
  8. customremoval of most of the benzyl alcohol

Sources & evidence

ORD record
ord-63b90180cec049d3866b4f650fb44c8e
Source dataset
uspto-grants-2002_03
Patent number
US06358985B1

Reaction notes

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