Iodine → Benzhydrol

HRID 2375138Notes

Reaction equation

HRID 2375138 reaction equation
C(O[C:4]1[CH:9]=[CH:8][C:7](Br)=[CH:6][CH:5]=1)C.[Mg].II.[CH2:14]([O:21]C1C=CC=CC=1C=O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[Cl-].[NH4+]>O1CCCC1.O>[C:15]1([CH:14]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)[OH:21])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

8

Reactant 5

HCID 807IodineHCID 25517Ammonium ChlorideHCID 685234-BromophenetoleHCID 3447842-(Benzyloxy)benzaldehydeHCID 5462224Magnesium

Product 1

HCID 7037BenzhydrolYield 178%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A Grignard reagent was prepared from 4-ethoxybromo-benzene (1.5 g), magnesium (0.19 g), a catalytic amount of iodine and tetrahydrofuran (2 mL) in the usual manner. To the obtained Grignard reagent solution was added dropwise a solution of 2-benzyloxybenzaldehyde (1.1 g) in tetrahydrofuran (15 mL), and the mixture was stirred at room temperature for 30 minutes. To the reaction mixture were added a saturated aqueous ammonium chloride solution (10 mL) and water (20 mL), and the mixture was extracted with ethyl acetate (100 mL). The extract was washed with water (20 mL) and brine (20 mL), and dried over anhydrous sodium sulfate. Thereafter, the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=5/1) to give a diphenylmethanol compound (1.7 g). The obtained diphenylmethanol compound (1.7 g) was dissolved in ethanol (25 mL). To the solution were added concentrated hydrochloric acid (0.42 mL) and a catalytic amount of 10% palladium-carbon, and the mixture was stirred under a hydrogen atmosphere at room temperature for 18 hours. The catalyst was removed by filtration, and the filtrate was concentrated under reduced pressure. To the residue was added ethyl acetate (100 mL), and the mixture was washed with a saturated aqueous sodium hydrogen carbonate solution (30 mL) and brine (30 mL). The organic layer was dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=8/1) to give 2-(4-ethoxybenzyl)phenol (0.85 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate (100 mL)
  2. washThe extract was washed with water (20 mL) and brine (20 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThereafter, the solvent was removed under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-7c35b1cf241146cf8a5158516f55df7c
Source dataset
uspto-grants-2008_12
Patent number
US07465712B2

Reaction notes

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