Benzyl Bromide → {2-Chloro-6-[(phenylmethyl)oxy]phenyl}methanol

HRID 1946297Notes

Reaction equation

HRID 1946297 reaction equation
[Cl:1][C:2]1[C:3]([CH2:9][OH:10])=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[OH-].[Na+].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:3]=1[CH2:9][OH:10]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 14798Sodium HydroxideHCID 541018233-Chloro-2-(hydroxymethyl)phenol

Product 1

HCID 28945839{2-Chloro-6-[(phenylmethyl)oxy]phenyl}methanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3-chloro-2-(hydroxymethyl)phenol (for a preparation see Intermediate 6)(1.37 g, 8.62 mmol) in absolute ethanol (30 ml) was added 2 M sodium hydroxide (4.74 ml, 9.49 mmol) and then benzyl bromide (1.03 ml, 8.62 mmol, Aldrich). The solution was stirred at ambient temperature for 3 days under nitrogen. The solvent was removed under reduced pressure to leave an aqueous suspension. The aqueous residue was partitioned between 2 M aqueous sodium hydroxide (40 ml) and ethyl acetate (60 ml). The phases were separated and the aqueous phase extracted with ethyl acetate (40 ml). The combined organic extracts were dried (MgSO4), filtered and the solvent removed under reduced pressure to give the title compound as a very pale brown oil (1.87 g); LCMS: (System 1) (M-H)−=247, tRET=3.20 min.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customto leave an aqueous suspension
  3. customThe aqueous residue was partitioned between 2 M aqueous sodium hydroxide (40 ml) and ethyl acetate (60 ml)
  4. customThe phases were separated
  5. extractionthe aqueous phase extracted with ethyl acetate (40 ml)
  6. dry with materialThe combined organic extracts were dried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-ceb409b8b2494cb6b95b42a254eb24bb
Source dataset
uspto-grants-2013_03
Patent number
US08399436B2

Reaction notes

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