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

HRID 337191
Notes
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Reaction equation

HRID 337191 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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-53e03c4968f94623a0aa01cae23e16bf
Source dataset
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08889722B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes