Hydrochloric Acid → HCID 12395598, compound

HRID 1579630Notes

Reaction equation

HRID 1579630 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-bromohexanoyl chloride (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.) made acidic with hydrochloric acid. The organic phase is separated washed with water, 2% sodium hydroxide and 1.0 M hydrochloric acid. The methylene chloride is evaporated at reduced pressure. The resulting oil is dissolved in ether, dried over magnesium sulfate, evaporated to 200 ml. and treated with hexane (600 ml.) to afford 2,3-dichloro-4-(6-bromohexanoyl) anisole which melts at 52°-53°C.

Workup

  1. customThe organic phase is separated
  2. washwashed with water, 2% sodium hydroxide and 1.0 M hydrochloric acid
  3. customThe methylene chloride is evaporated at reduced pressure
  4. dissolutionThe resulting oil is dissolved in ether
  5. dry with materialdried over magnesium sulfate
  6. customevaporated to 200 ml
  7. additionand treated with hexane (600 ml.)

Sources & evidence

ORD record
ord-b2e4a4c9372a494a806a6781e6b1e06b
Source dataset
uspto-grants-1976_01
Patent number
US03931239

Reaction notes

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