Etofenprox → 3-Phenoxytoluene

HRID 2351808Notes

Reaction equation

HRID 2351808 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([CH3:28])([CH3:27])[CH2:11][O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:15]=2)=[CH:6][CH:5]=1)[CH3:2].ClC1C=C(C(C)(C)COCC2C=CC=C(OC3C=CC=CC=3)C=2)C=CC=1OCC>C1C=CC=CC=1>[O:20]([C:16]1[CH:15]=[C:14]([CH3:13])[CH:19]=[CH:18][CH:17]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1.[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([CH3:27])([CH3:28])[CH2:11][OH:12])=[CH:6][CH:5]=1)[CH3:2]

Participants

5

Reactant 2

HCID 71245EtofenproxHCID 30671833-Chloro-4-ethoxyneophyl 3-phenoxybenzyl ether

Product 2

HCID 191653-PhenoxytolueneHCID 1585252-(4-Ethoxyphenyl)-2-methylpropanol

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The reaction mixture was cooled to room temperature and the residual pressure was released, and 120 ml of benzene was added into the autoclave to dissolve the oil layer. Then, the insoluble substance was removed by filtration, and the mother liquid was washed with 30 ml of benzene, sufficiently shaken and allowed to stand still to cause phase separation and give a benzene layer. The benzene layer was washed with 120 ml of water three times and benzene was removed by distillation under reduced pressure to give an oily product. From the results of the analysis of the oily product by gas chromatography according to the internal standard method, it was found that the oily product comprised 98.5% of 3-phenoxybenzyl 2-(4-ethoxyphenyl)-2-methylpropyl ether and 0.5% of unreacted starting 3-phenoxybenzyl 2-(3-chloro-4-ethoxyphenyl)-2-methylpropyl ether, and that the content of each of 3-phenoxytoluene and 4-ethoxyneophyl alcohol formed by cleaving of the ether linkage was lower than 0.3%. The amount of the obtained oily product was 53.6 g and the yield was 96.0%.

Workup

  1. dissolutionto dissolve the oil layer
  2. customThen, the insoluble substance was removed by filtration
  3. washthe mother liquid was washed with 30 ml of benzene
  4. customphase separation
  5. customgive a benzene layer
  6. washThe benzene layer was washed with 120 ml of water three times and benzene
  7. customwas removed by distillation under reduced pressure
  8. customto give an oily product
  9. customFrom the results of the analysis of the oily product by gas chromatography

Sources & evidence

ORD record
ord-f9ecd808af524dcf8801503ac4ddf198
Source dataset
uspto-grants-1989_10
Patent number
US04873373

Reaction notes

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