Water → HCID 21255618, compound

HRID 636763Notes

Reaction equation

HRID 636763 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:19]=[C:20]([CH:25]=[CH:26][C:27]=3[CH3:28])[C:21]([O:23][CH3:24])=[O:22])=[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:19]=[C:20]([CH:25]=[CH:26][C:27]=3[CH2:28][Br:48])[C:21]([O:23][CH3:24])=[O:22])=[O:15])[CH:5]=[CH:4][C:3]1=2

Participants

7

Reactant 4

HCID 962WaterHCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 21255601HCID 21255601, compound

Product 1

HCID 21255618HCID 21255618, compound

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of methyl 3-[(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthoyl)methyloxy]-4-methylbenzoate (7.02 g, 16.7 mmol), benzoyl peroxide (0.02 g) and N-bromosuccinimide (4.28 g, 24 mmol) in carbon tetrachloride (370 ml) was heated at reflux and irradiated with a 1000 W lamp for forty five minutes. 350 ml of water and 250 ml of dichloromethane were added. After separation of the phases once settling had taken place, the organic phase was washed twice with 350 ml of water and dried over magnesium sulfate. After concentration on a rotary evaporator at 40° C. under vacuum, the three products obtained were purified by flash chromatography (CH2Cl2) and then by HPLC (70% CH2Cl2, 30% heptane). The properties of the monobromo benzyl compound were as follows:

Workup

  1. temperatureat reflux
  2. customirradiated with a 1000 W lamp for forty five minutes
  3. customAfter separation of the phases
  4. washthe organic phase was washed twice with 350 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 three products obtained
  9. customwere purified by flash chromatography (CH2Cl2)

Sources & evidence

ORD record
ord-6f0c393150434f9797593a50d3aeb768
Source dataset
uspto-grants-2001_02
Patent number
US06194450B1

Reaction notes

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