2-Chloroethanol → Benzene, (2-chloroethoxy)-

HRID 854160Notes

Reaction equation

CN(C)[CH2:3][CH2:4][O:5][C:6]1[CH:13]=[CH:12][C:9](CN)=[CH:8][CH:7]=1.C1(O)C=CC=CC=1.C([Cl:25])CO.O(CCO)C1C=CC=CC=1.S(Cl)(Cl)=O>>[O:5]([CH2:4][CH2:3][Cl:25])[C:6]1[CH:13]=[CH:12][CH:9]=[CH:8][CH:7]=1

Participants

Reactant 5

HCID 342-Chloroethanol

HCID 996Phenol2×

HCID 24386Thionyl Chloride

HCID 31236Phenoxyethanol

HCID 88349p-(2-(Dimethylamino)ethoxy)benzylamine

Product 1

HCID 12156Benzene, (2-chloroethoxy)-

Procedure

FR 2549828 discloses a multistage process for preparing 4-[2-(dimethylamino)ethoxy]benzylamine starting from phenol. Reaction of phenol with ethylenechlorohydrin initially delivers 2-phenoxyethanol which is reacted with thionyl chloride to give 2-phenoxyethyl chloride. After distilling this intermediate, it is reacted with acetamide and paraformaldehyde and then treated with mineral acid to give N-(2-chloroethoxybenzyl)acetamide. Reaction with dimethylamine then leads to N-[2-(dimethylamino)-ethoxy]acetamide, from which the desired product is released by acid hydrolysis. The process disclosed which has 6 separate process steps and an overall yield of 50% based on the phenol used is uneconomic.

Sources & evidence

ORD record: ord-fb36bd055a104bbbb2409225411ad0ca
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07256312B2

Reaction notes

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