HCID 59316794, compound → 3-Bromo-4-propan-2-yloxybenzoic acid

HRID 2189745

Reaction equation

HRID 2189745 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][C:13]=1[O:14][CH:15]([CH3:17])[CH3:16])[C:5]([O:7]C(C)C)=[O:6]>C(O)C.[OH-].[Na+]>[Br:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][C:13]=1[O:14][CH:15]([CH3:17])[CH3:16])[C:5]([OH:7])=[O:6]

Participants

4

Reactant 1

HCID 59316794HCID 59316794, compound

Product 1

HCID 166412393-Bromo-4-propan-2-yloxybenzoic acidYield 90.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 1-methylethyl 3-bromo-4-[(1-methylethyl)oxy]benzoate (D14) (2.36 g, 7.84 mmol) in ethanol (100 mL) and aqueous sodium hydroxide (2M, 39 mL) was heated to reflux for 5 h. The reaction mixture was concentrated in vacuo and partitioned between ethyl acetate (125 mL) and water (125 mL), the latter acidified with 2M HCl (40 mL). The aqueous layer was extracted with further ethyl acetate (70 mL) and the combined organic extracts dried (phase separator) and concentrated in vacuo to give the title compound as an off-white solid (1.83 g, 7.06 mmol). MS (ES): C10H11BrO3 requires 258, 260; found 257, 259 (M−H+).

Workup

  1. temperatureto reflux for 5 h
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. custompartitioned between ethyl acetate (125 mL) and water (125 mL)
  4. extractionThe aqueous layer was extracted with further ethyl acetate (70 mL)
  5. customthe combined organic extracts dried (phase separator)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-23edd38d5d7844e28be7704ea492dfc1
Source dataset
uspto-grants-2012_12
Patent number
US08324254B2

Linked notes

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