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

HRID 2163717Notes

Reaction equation

HRID 2163717 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 (2.1g; 0.01 mole), 1-bromo-3-phenoxypropane (2.15g; 0.01 mole) and anhydrous potassium carbonate (1.52g; 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 6.5Hz); 6.16 (3H,s); 6.11 (3H, s); 5.86 (2H, t, J 6.5Hz; 5.78 (2H, t, J 6.7Hz); 3.20-2.55 (7H, m); 2.19 (1H, d, J 8.5Hz); (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-bb163d9eed164b1a918d4ec6b0679a5e
Source dataset
uspto-grants-1979_01
Patent number
US04136192

Reaction notes

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