Etofenprox → 3-Phenoxytoluene

HRID 2351811Notes

Reaction equation

HRID 2351811 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>[C].[Pd]>[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 178418390HCID 178418390, compoundCatalyst

Procedure

The dechlorination reaction was carried out in the same manner as in Example 1 except that 1.44 g of 10%-palladium-alumina (100% dry) was used instead of the 5%-palladium-carbon used as the hydrogenation catalyst in Example 1, and an oily product was obtained by carrying out the post-treatment in the same manner as in Example 1. 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 97.4% 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 0.7%. The amount of the obtained oily product was 52.0 g and the yield was 93.2%.

Workup

  1. customThe dechlorination reaction
  2. customan oily product was obtained
  3. customFrom the results of the analysis of the oily product by gas chromatography

Sources & evidence

ORD record
ord-ee120250919e49218973cd57aed86b7a
Source dataset
uspto-grants-1989_10
Patent number
US04873373

Reaction notes

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