Sodium Hydroxide → 2-(Benzyloxy)-4-bromo-5-methylbenzoic Acid

HRID 2204682Notes

Reaction equation

HRID 2204682 reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([C:9](=[O:11])C)=[C:4]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:3]=1.[OH-:20].[Na+].BrBr>O1CCOCC1.O>[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([C:9]([OH:11])=[O:20])=[C:4]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:3]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 24408BromineHCID 66611357HCID 66611357, compound

Product 1

HCID 666115892-(Benzyloxy)-4-bromo-5-methylbenzoic Acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1-{4-bromo-5-methyl-2-[(phenylmethyl)oxy]phenyl}ethanone (may be prepared as described in Description 11; 607 mg, 1.90 mmol) in 1,4-dioxane (10 ml) was added sodium hydroxide (761 mg, 19.02 mmol) in water (10 ml). The solution was cooled to 0° C. and bromine (0.29 ml, 5.71 mmol) was added. The mixture was stirred for 10 minutes at 0° C. and then at room temperature for one hour. The dioxane was removed under reduced pressure and the residue acidified to pH=2 using 2N HCl. The mixture was extracted with ethyl acetate (3×20 ml), dried (MgSO4) and the solvent removed in vacuo to yield the title compound. 611 mg.

Workup

  1. waitat room temperature for one hour
  2. customThe dioxane was removed under reduced pressure
  3. extractionThe mixture was extracted with ethyl acetate (3×20 ml)
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-bad6d1dae2a74c609d1315159d1fcbac
Source dataset
uspto-grants-2016_06
Patent number
US09365551B2

Reaction notes

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