Sulfuric Acid → HCID 4581090, compound

HRID 1651301Notes

Reaction equation

HRID 1651301 reaction equation
[CH2:1]([CH:3]1[O:5][CH2:4]1)[Cl:2].[CH3:6][O:7][CH2:8][CH2:9][OH:10].S(=O)(=O)(O)O>CCOCC>[Cl:2][CH2:1][CH:3]([OH:5])[CH2:4][O:10][CH2:9][CH2:8][O:7][CH3:6]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 7835EpichlorohydrinHCID 80192-Methoxyethanol

Product 1

HCID 4581090HCID 4581090, compoundYield 43,929.898%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To 25 g (0.27 mmol) of epichlorohydrin, 20.8 g (0.27 mmol) of methylcellosolve and 0.1 ml of conc. sulfuric acid were added and reacted for 10 hours at 100° C. After the reaction, 500 ml of ether was added and washed with saturated sodium hydrogen carbonate solution and with saturated sodium chloride solution. The ether phase was dried on magnesium sulfate, filtered and concentrated to give 20 g of 1-chloro-2-hydroxy-3-(2'-methoxyethoxy)propane. 1H-NMR (CDCl3): δ=3.40 (3H, s, --OCH3), 3.45-3.82 (9H, m, H1, H3, H1', H2', --OH), 3.84-4.18 (1H, m, H2).

Workup

  1. customreacted for 10 hours at 100° C
  2. additionwas added
  3. washwashed with saturated sodium hydrogen carbonate solution and with saturated sodium chloride solution
  4. dry with materialThe ether phase was dried on magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0fecd867da1544fcb30e2444ea13c434
Source dataset
uspto-grants-1990_05
Patent number
US04927941

Reaction notes

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