Lithium Hydroxide → 4-(3-bromophenyl)oxane-4-carboxylic Acid

HRID 216226Notes

Reaction equation

HRID 216226 reaction equation
[OH-].[Li+].C[O:4][C:5]([C:7]1([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([Br:19])[CH:14]=2)[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1)=[O:6]>CO.O.O>[Br:19][C:15]1[CH:14]=[C:13]([C:7]2([C:5]([OH:6])=[O:4])[CH2:12][CH2:11][O:10][CH2:9][CH2:8]2)[CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 67091038Methyl 4-(3-bromophenyl)tetrahydro-2H-pyran-4-carboxylate

Product 1

HCID 112546334-(3-bromophenyl)oxane-4-carboxylic AcidYield 93.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 22242641Methanol--water (1/1)Solvent

Conditions

Temperature
65 °C

Procedure

Lithium hydroxide (0.21 g, 5.01 mmol) is added to a solution of 4-(3-bromo-phenyl)-tetrahydro-pyran-4-carboxylic acid methyl ester (0.5 g, 1.67 mmol) in methanol/water (8 mL, 3:1) and the reaction mixture is stirred for 5 hours at 65° C. The mixture is diluted with water and the volatiles are removed in vacuo. The aqueous is extracted once with diethyl ether, acidified to pH 2, and extracted twice with ethyl acetate. The combined extracts is dried over magnesium sulfate, filtered and concentrated in vacuo to afford 4-(3-bromo-phenyl)-tetrahydro-pyran-4-carboxylic acid (445 mg) sed in the next step without further purification. LCMS: RT=1.9 minutes; MS: 283 (M−H).

Workup

  1. customthe volatiles are removed in vacuo
  2. extractionThe aqueous is extracted once with diethyl ether
  3. extractionextracted twice with ethyl acetate
  4. dry with materialThe combined extracts is dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a102a90112c14852a9fdb386d7fb0317
Source dataset
uspto-grants-2012_06
Patent number
US08193183B2

Reaction notes

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