Lithium hydroxide, monohydrate → 4-(3-Bromopropoxy)benzoic acid

HRID 2108365Notes

Reaction equation

HRID 2108365 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12]C)=[O:11])=[CH:8][CH:7]=1.O.[OH-].[Li+]>C1COCC1.O.CO.O>[Br:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([OH:12])=[O:11])=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 3709742Methyl 4-(3-bromopropoxy)benzoate

Product 1

HCID 176070514-(3-Bromopropoxy)benzoic acidYield 71.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21892291Methanol tetrahydrofuran waterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 107A (2.44 g, 8.9 mmol) and lithium hydroxide monohydrate (750 mg, 17.9 mmol) in THF-H2O-MeOH (15:7:7, 29 mL) was stirred at 60° C. for 2.0 hr. After cooling to room temperature, the reaction mixture was diluted with water (30 mL) and concentrated in vacuo to remove most organic solvents. The mixture was washed with 1:1 mixture of ethyl acetate-ether and the aqueous layer was acidified with 2.0 N HCl to pH 5.0. The precipitate was collected by filtration, rinsed with water and dried under high vacuum to give 107B as a crystalline solid (1.64 g, 71%).

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationconcentrated in vacuo
  3. customto remove most organic solvents
  4. washThe mixture was washed with 1:1 mixture of ethyl acetate-ether
  5. filtrationThe precipitate was collected by filtration
  6. washrinsed with water
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-77ee2031480a469fafe1b362e9c4e491
Source dataset
uspto-grants-2009_04
Patent number
US07514435B2

Reaction notes

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