Hydrochloric Acid → 4-Methoxyphenyl (4-(4-methyl-3-pentenyl)-3-cyclohexenyl)methyl ketone

HRID 2227101Notes

Reaction equation

HRID 2227101 reaction equation
[CH3:1][C:2]([CH3:16])=[CH:3][CH2:4][CH2:5][C:6]1[CH2:11][CH2:10][CH:9]([CH2:12][C:13](Cl)=[O:14])[CH2:8][CH:7]=1.[C:17]1([O:23][CH3:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.Cl>ClCCl>[CH3:1][C:2]([CH3:16])=[CH:3][CH2:4][CH2:5][C:6]1[CH2:11][CH2:10][CH:9]([CH2:12][C:13]([C:20]2[CH:21]=[CH:22][C:17]([O:23][CH3:24])=[CH:18][CH:19]=2)=[O:14])[CH2:8][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7519AnisoleHCID 18471799(4-(4-Methyl-3-pentenyl)-3-cyclohexenyl)acetyl chloride

Product 1

HCID 867582894-Methoxyphenyl (4-(4-methyl-3-pentenyl)-3-cyclohexenyl)methyl ketone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of acid chloride 2C (R=4-Methyl-3-pentenyl) (10 g) in anhydrous dichloromethane (100 mL) is added dropwise to a mixture of ferric chloride (7.8 g) and anisole 2D (4.5 g) in dichloromethane (175 mL), cooled in an ice/ethanol bath. The resulting mixture is gradually warmed to room temperature and stirred overnight. The mixture is poured into 25% HCl (150 mL) and stirred for 30 minutes. The aqueous layer is extracted with dichloromethane, and the combined organic layers are sequentially washed with water, sodium bicarbonate, and water, then dried over magnesium sulfate. The solution is concentrated in vacuo.

Workup

  1. temperaturecooled in an ice/ethanol bath
  2. stirringstirred for 30 minutes
  3. extractionThe aqueous layer is extracted with dichloromethane
  4. washthe combined organic layers are sequentially washed with water, sodium bicarbonate, and water
  5. dry with materialdried over magnesium sulfate
  6. concentrationThe solution is concentrated in vacuo

Sources & evidence

ORD record
ord-e3313ea46cd7402aa009ca69600977fe
Source dataset
uspto-grants-2002_07
Patent number
US06413448B1

Reaction notes

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