Hydrochloric Acid → (RS)-2-bromo-6-(1-hydroxyheptyl)anisole

HRID 41526

Reaction equation

HRID 41526 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[C:3]=1[O:9][CH3:10].[CH:11](=[O:18])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].Cl>C1COCC1>[Br:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([CH:11]([OH:18])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[C:3]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8130HeptanalHCID 181584Benzene, 1,3-dibromo-2-methoxy-

Product 1

HCID 59544889(RS)-2-bromo-6-(1-hydroxyheptyl)anisoleYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

To a THF solution of 2,6-dibromoanisole (10 g, 37.6 mmol) was added Mg (0.90 g, 37.6 mmol), and the mixture was heated and stirred at 40° C. Under ice-cooling, n-heptanal (47.2 g, 41.3 mmol) was added dropwise. Aqueous hydrochloric acid solution was added to the reaction mixture, this was extracted with ethyl acetate, and the solvent was distilled off to obtain 8.95 g of a compound (1).

Workup

  1. temperaturethe mixture was heated
  2. temperatureUnder ice-cooling
  3. extractionthis was extracted with ethyl acetate
  4. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-0586628f68394c568875f29b5148eba6
Source dataset
uspto-grants-2013_09
Patent number
US08530668B2

Linked notes

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