3-Phenoxybenzyl chloride → 3-Phenoxybenzyl chloride

HRID 434619Notes

Reaction equation

HRID 434619 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH2:11]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:16]([C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=1)[CH:26](Cl)[Cl:27])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[O:32]([C:39]1[CH:40]=[C:41]([C:45](Cl)([Cl:47])[Cl:46])[CH:42]=[CH:43][CH:44]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>>[O:1]([C:8]1[CH:9]=[C:10]([CH3:11])[CH:13]=[CH:14][CH:15]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1.[O:16]([C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=1)[CH2:26][Cl:27])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1.[O:32]([C:39]1[CH:40]=[C:41]([CH:42]=[CH:43][CH:44]=1)[CH:45]([Cl:46])[Cl:47])[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

6

Reactant 3

HCID 932913-Phenoxybenzyl chlorideHCID 1046311-(Dichloromethyl)-3-phenoxybenzeneHCID 12765855HCID 12765855, compound

Product 3

HCID 191653-PhenoxytolueneYield 41%HCID 932913-Phenoxybenzyl chlorideYield 45.7%HCID 1046311-(Dichloromethyl)-3-phenoxybenzeneYield 12.1%

Procedure

Exactly the same procedure as in Example 19 is followed except that 1 g of N-diethyleneoxy-2-benzothiazolyl sulfenamide is used in place of 1 g of N-pentamethylenedithiocarbamic acid piperidinium salt. The result shows 2.1% of m-phenoxybenzyl chloride, 95.6% of m-phenoxybenzal chloride, 1.8% of m-phenoxyphenyl trichloromethane and 0.5% of nuclear-chlorinated products. The similar reaction without the above sulfenamide gives 41.0% of m-phenoxytoluene, 45.7% of m-phenoxybenzyl chloride, 12.1% of m-phenoxybenzal chloride and 1.2% of nuclear-chlorinated compounds.

Sources & evidence

ORD record
ord-71d98d45c4ee43ea8e2f98a554c36462
Source dataset
uspto-grants-1983_08
Patent number
US04399075

Reaction notes

Loading…