Hydrochloric Acid → HCID 12395598, compound

HRID 2083465Notes

Reaction equation

HRID 2083465 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[O:9][CH3:10].[Br:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17](Cl)=[O:18].[Cl-].[Al+3].[Cl-].[Cl-].Cl>C(Cl)Cl>[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([C:17](=[O:18])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][Br:11])[CH:5]=[CH:4][C:3]=1[O:9][CH3:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 161262,3-DichloroanisoleHCID 898486-Bromohexanoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 12395598HCID 12395598, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

A stirred mixture of 2,3-dichloroanisole (89 g., 0.50 mole) and 6-bromohexanoylchloride (120 g., 0.59 mole) in methylene chloride (500 ml.) is cooled to 5° C. and treated with aluminum chloride (74 g., 0.56 mole) in portions during a one-half hour period. The reaction mixture is kept at 25° C. for 18 hours then poured into ice water (1 l.) containing hydrochloric acid (100 ml.) the organic phase is separated, washed with water, 2% sodium hydroxide and dilute hydrochloric acid. The methylene chloride is evaporated at reduced pressure. The crude product is dissolved in ether (200 ml.), dried over magnesium sulfate, filtered and treated with hexane (600 ml.) affording 2,3-dichloro-4-(6-bromohexanoyl)anisole which melts at 52°-53° C.

Workup

  1. customis separated
  2. washwashed with water, 2% sodium hydroxide and dilute hydrochloric acid
  3. customThe methylene chloride is evaporated at reduced pressure
  4. dissolutionThe crude product is dissolved in ether (200 ml.)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. additiontreated with hexane (600 ml.)

Sources & evidence

ORD record
ord-026fcff5fb094900b3c9829c15dd057e
Source dataset
uspto-grants-1978_04
Patent number
US04085219

Reaction notes

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