Monobenzone → HCID 66957184, compound

HRID 2066624Notes

Reaction equation

HRID 2066624 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Cl[CH2:23][C:24]([CH3:26])=[CH2:25]>CC(C)=O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][CH2:25][C:24]([CH3:26])=[CH2:23])=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7638MonobenzoneHCID 112413-Chloro-2-methyl-1-propeneHCID 11430Potassium Carbonate

Product 1

HCID 66957184HCID 66957184, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
58 °C

Procedure

A mixture of 4-(benzyloxy)phenol (2.01 g, 10.1 mmol), K2CO3 (1.60 g, 11.6 mmol) and 3-chloro-2-methylpropene (93) (2.00 mL, 20.4 mmol) in anhydrous acetone (2.5 mL) was stirred in a sealed vial at 58° C. for 24 h. The resulting mixture was filtered, washing with CH2Cl2, and then the filtrate was evaporated to dryness and the residue was chromatographed on silica gel. Elution with petroleum ether firstly gave foreruns, and then further elution with 25% CH2Cl2/petroleum ether gave 1-(benzyloxy)-4-[(2-methyl-2-propenyl)oxy]benzene (94) (Karrer, F. DE 2312518) (1.74 g, 68%) as a white solid: mp (CH2Cl2/hexane) 62-64° C.; 1H NMR (CDCl3) δ 7.45-7.29 (m, 5H), 6.90 (dt, J=9.3, 2.8 Hz, 2H), 6.85 (dt, J=9.3, 2.8 Hz, 2H), 5.08 (m, 1H), 5.01 (s, 2H), 4.79 (m, 1H), 4.38 (s, 2H), 1.82 (s, 3H).

Workup

  1. filtrationThe resulting mixture was filtered
  2. washwashing with CH2Cl2
  3. customthe filtrate was evaporated to dryness
  4. customthe residue was chromatographed on silica gel
  5. washElution with petroleum ether firstly gave foreruns
  6. washfurther elution with 25% CH2Cl2/petroleum ether

Sources & evidence

ORD record
ord-3e43dab55ae949399033edbd7fc69eaa
Source dataset
uspto-grants-2012_10
Patent number
US08293734B2

Reaction notes

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