Potassium Carbonate → Dimethyl 4-(3-phenoxypropoxy)phthalate

HRID 2057598

Reaction equation

HRID 2057598 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:12]([O:14][CH3:15])=[O:13])[C:5](=[CH:10][CH:11]=1)[C:6]([O:8][CH3:9])=[O:7].Br[CH2:17][CH2:18][CH2:19][O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[O:20]([CH2:19][CH2:18][CH2:17][O:1][C:2]1[CH:3]=[C:4]([C:12]([O:14][CH3:15])=[O:13])[C:5](=[CH:10][CH:11]=1)[C:6]([O:8][CH3:9])=[O:7])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 68522Benzene, (3-bromopropoxy)-HCID 89726Dimethyl 4-hydroxyphthalate

Product 1

HCID 20331397Dimethyl 4-(3-phenoxypropoxy)phthalate

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of dimethyl 4-hydroxyphthalate (2.1 g; 0.01 mole), 1-bromo-3-phenoxypropane (2.15 g; 0.01 mole) and anhydrous potassium carbonate (1.52 g; 0.015 mole) in dry butanone (30 ml) was stirred at reflux overnight and the cooled mixture filtered. Evaporation in vacuo afforded the title compound in quantitative yield. νmax (film) 1730, 1605 cm-1 ; τ(CDCl3) 7.77 (2H, quintet, J 6.5 Hz); 6.16 (3H,s); 6.11 (3H, s); 5.86 (2H, t, J 6.5 Hz); 5.78 (2H, t, J 6.7 Hz); 3.20°-2.55 (7H, m); 2.19 (1H, d, J 8.5 Hz); (Found; C, 65.98; H, 5.89; C19H20O6 requires; C, 66.27; H, 5.85%).

Workup

  1. temperatureat reflux overnight
  2. filtrationthe cooled mixture filtered
  3. customEvaporation in vacuo

Sources & evidence

ORD record
ord-57f71a2ff20043b7ac4eb965171ced47
Source dataset
uspto-grants-1980_07
Patent number
US04211791

Linked notes

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