Acetone → Dimethyl 5-bentyloxy-isophthalate

HRID 328871Notes

Reaction equation

HRID 328871 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:12]([O:14][CH3:15])=[O:13])[CH:5]=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C([O-])([O-])=O.[K+].[K+].CC(C)=O>C1CCCCC1>[CH2:16]([O:1][C:2]1[CH:11]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH:5]=[C:4]([CH:3]=1)[C:12]([O:14][CH3:15])=[O:13])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 830651,3-Benzenedicarboxylic acid, 5-hydroxy-, 1,3-dimethyl ester

Product 1

HCID 7643390Dimethyl 5-bentyloxy-isophthalate

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

A mixture of 156 g (0.743 mole) of dimethyl 5-hydroxyisophthalate, 171 g (1 mole) of benzylbromide and 138 g (1 mole) of K2CO3 in 1 l. of acetone was refluxed for 18 hours. The reaction mixture was evaporated to a residue which was extracted with hot cyclohexane to give the crystalline product in a quantitive yield upon cooling. The analytical sample was obtained by recrystallization from cyclohexane, mp. 94-95° .

Workup

  1. customThe reaction mixture was evaporated to a residue which
  2. extractionwas extracted with hot cyclohexane
  3. customto give the crystalline product in
  4. customa quantitive yield
  5. temperatureupon cooling

Sources & evidence

ORD record
ord-f8c1f09a9e7149af941ca69ab6ea4609
Source dataset
uspto-grants-1977_04
Patent number
US04018825

Reaction notes

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