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Ethanol → ethyl (chloroethoxy)formate

HRID 1488875
Notes
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Reaction equation

HRID 1488875 reaction equation
Cl[C:2]([O:4][CH2:5][CH2:6][Cl:7])=[O:3].[CH2:8]([OH:10])[CH3:9].N1C=CC=CC=1>C(Cl)Cl>[C:2](=[O:3])([O:4][CH2:5][CH2:6][Cl:7])[O:10][CH2:8][CH3:9]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 702EthanolHCID 1049PyridineHCID 123052-Chloroethyl chloroformate

Product 1

HCID 12238111ethyl (chloroethoxy)formateYield 74.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of chloroethyl chloroformate (23.16 g, 0.162 mol) and ethanol (7.45 g, 0.162 mol) in methylene chloride (200 ml), pyridine (12.82 g, 0.162 mol) was added at 0° C. After 10 min at 0° C. and 21 hours at 25° C. the reaction mixture was washed with aqueous hydrochloric acid (100 ml), aqueous saturated sodium hydrogen carbonate (100 ml) and water (100 ml). The solvent was removed under reduced pressure after drying (MgSO4), giving 18.5 g (74%) of the intermediate ethyl chloroethyl carbonate as a crude product.

Workup

  1. wash21 hours at 25° C. the reaction mixture was washed with aqueous hydrochloric acid (100 ml), aqueous saturated sodium hydrogen carbonate (100 ml) and water (100 ml)
  2. customThe solvent was removed under reduced pressure
  3. dry with materialafter drying (MgSO4)

Sources & evidence

ORD record
ord-618e3eb8611b41aba61114ec66b17a41
Source dataset
uspto-grants-1997_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05676925

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes