Ethylene Glycol → Benzoic acid, 4-((1,1-dimethyl-2-((3-phenoxyphenyl)methoxy)ethyl))-, ethyl ester

HRID 434535Notes

Reaction equation

HRID 434535 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]([CH3:27])([CH3:26])[CH2:10][O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:14]=2)=[CH:5][CH:4]=1)#N.[OH-:28].[K+].Cl.[CH2:31](O)[CH2:32][OH:33]>O>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]([CH3:27])([CH3:26])[CH2:10][O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:14]=2)=[CH:5][CH:4]=1)([O:33][CH2:32][CH3:31])=[O:28].[C:4]([C:5]1[CH:1]=[CH:3][CH:8]=[CH:7][C:6]=1[C:9]([CH3:26])([CH3:27])[CH2:10][O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:14]=1)([OH:33])=[O:28]

Participants

7

Reactant 4

HCID 174Ethylene GlycolHCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 3067160Benzonitrile, 4-(1,1-dimethyl-2-((3-phenoxyphenyl)methoxy)ethyl)-

Product 2

HCID 3067190Benzoic acid, 4-((1,1-dimethyl-2-((3-phenoxyphenyl)methoxy)ethyl))-, ethyl esterHCID 20247009HCID 20247009, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
130 °C

Procedure

3-Phenoxybenzyl 2-(4-carboethoxyphenyl)-2-methylpropyl ether was synthesized according to the following procedures. (1) A mixture of 3.5 g of 3-phenoxybenzyl 2-(4-cyanophenyl)-2-methylpropyl ether, 7.0 g of potassium hydroxide, 7.0 g of water and 20 ml of ethylene glycol was stirred at 130° C. for 4.0 hours. The mixture was cooled to room temperature, and water was added and the mixture was made acidic by addition of hydrochloric acid. Then, the mixture was extracted with ether, and the ether extract was washed with water, dried over Na2SO4, and evaporated to give 3.1 g of 3-phenoxybenzyl 2-(carboxyphenyl)-2-methylpropyl ether (mp. 98.5°-102.5° C.). (2) A mixture of 1.0 g of 3-phenoxybenzyl 2-(4-carboxyphenyl)-2-methylpropyl ether, 0.6 g of phosphorus pentachloride and 15 ml of benzene was treated at 70° to 80° C. for 30 minutes, and the solvent was removed by distillation under reduced pressure. The obtained crude acid chloride was dissolved in 10 ml of benzene and the solution was added dropwise to a mixed solution of 5 ml of ethanol, 1 ml of pyridine and 30 ml of benzene at room temperature. The mixture was allowed to stand for 30 minutes, washed with water and dried over Na2SO4, and evaporated under reduced pressure to give 1.3 g of a crude ester. The obtained crude ester was purified by column chromatography on 40 g of silica gel (benzene was used as eluent) to give 0.9 g of 3-phenoxybenzyl 2-(4-carboethoxyphenyl)-2-methylpropyl ether.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. extractionThen, the mixture was extracted with ether
  3. extractionthe ether extract
  4. washwas washed with water
  5. dry with materialdried over Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-7dc1677ebe6e46f8ac5802289f3516f1
Source dataset
uspto-grants-1983_08
Patent number
US04397864

Reaction notes

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