Acetic Acid → HCID 59463784, compound

HRID 1713344Notes

Reaction equation

HRID 1713344 reaction equation
[CH3:1][C:2]1([CH2:12][CH2:13][OH:14])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][CH2:4][CH2:3]1.[Br:15]Br.C(=O)([O-])[O-].[K+].[K+].[C:23]([OH:26])(=O)[CH3:24]>O>[Br:15][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[O:5][CH2:4][CH2:3][C:2]2([CH2:12][CH2:13][O:14][C:23](=[O:26])[CH3:24])[CH3:1]

Participants

6

Reactant 4

HCID 176Acetic Acid2×HCID 11430Potassium CarbonateHCID 24408BromineHCID 59463790HCID 59463790, compound

Product 1

HCID 59463784HCID 59463784, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2.5 g (13 mmol) of 2-(4-methylchroman-4-yl)ethanol in 15 mL of acetic acid was added 7.5 mL of a 2.7 M solution of bromine in acetic acid. After 30 minutes, the reaction was poured onto an ice cold slurry of potassium carbonate in water and extracted with diethyl ether. The combined organic fractions were dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was passed through a pad of silica gel using ethyl acetate-hexanes (0-30% gradient) to afford 3.6 g (90%) of acetic acid 2-(6-bromo-4-methylchroman-4-yl)ethyl ester as an oil. The ester was treated with 0.96 g (23 mmol) of lithium hydroxide in 45 mL of 4:1 mixture of methanol-water. After stirring overnight, the reaction was concentrated in vacuo to remove methanol and the remaining aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over magnesium sulfate, filtered, and concentrated in vacuo to afford 3 g (96%) of 2-(6-bromo-4-methylchroman-4-yl)ethanol as an oil.

Workup

  1. extractionextracted with diethyl ether
  2. dry with materialThe combined organic fractions were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-775fd9e011e447b69654a8de7cb7bd81
Source dataset
uspto-grants-2010_09
Patent number
US07795272B2

Reaction notes

Loading…