Water → HCID 21255625, compound

HRID 636764Notes

Reaction equation

HRID 636764 reaction equation
[CH3:1][C:2]1([CH3:29])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([C:14]([CH2:16][O:17][C:18]3[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][C:19]=3[CH3:28])=[O:15])[CH:5]=[CH:4][C:3]1=2.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[Br:48]N1C(=O)CCC1=O.O>C(Cl)(Cl)(Cl)Cl.ClCCl>[CH3:1][C:2]1([CH3:29])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]2[CH:7]=[C:6]([C:14]([CH2:16][O:17][C:18]3[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][C:19]=3[CH2:28][Br:48])=[O:15])[CH:5]=[CH:4][C:3]1=2

Participants

7

Reactant 4

HCID 962WaterHCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 21255612HCID 21255612, compound

Product 1

HCID 21255625HCID 21255625, compound

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of methyl 4-[(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthoyl)methyloxy]-3-methylbenzoate (3.73 g, 9.5 mmol), benzoyl peroxide (0.02 g) and N-bromosuccinimide (1.74 g, 9.8 mmol) in carbon tetrachloride (200 ml) was heated to reflux and irradiated with a 1000 W lamp for fifteen minutes. 300 ml of water and 150 ml of dichloromethane were added. After separation of the phases once settling had taken place, the organic phase was washed twice, with 250 ml of water, and dried over magnesium sulfate. After concentration on a rotary evaporator at 40° C. under vacuum, the product obtained was purified by flash chromatography (10% CH2Cl2, 90% heptane). Its properties were as follows:

Workup

  1. temperatureto reflux
  2. customirradiated with a 1000 W lamp for fifteen minutes
  3. customAfter separation of the phases
  4. washthe organic phase was washed twice, with 250 ml of water
  5. dry with materialdried over magnesium sulfate
  6. concentrationAfter concentration
  7. customon a rotary evaporator at 40° C. under vacuum
  8. customthe product obtained
  9. customwas purified by flash chromatography (10% CH2Cl2, 90% heptane)

Sources & evidence

ORD record
ord-ebb0995627f349709c46dcca96bfeaef
Source dataset
uspto-grants-2001_02
Patent number
US06194450B1

Reaction notes

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