Hydroquinone → benzene-1,4-diyl bis(chloroacetate)

HRID 1512966Notes

Reaction equation

HRID 1512966 reaction equation
[C:1]1([CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[OH:2].[Cl:9][CH2:10][C:11](Cl)=[O:12]>>[Cl:9][CH2:10][C:11]([O:2][C:1]1[CH:8]=[CH:7][C:5]([O:6][C:11](=[O:12])[CH2:10][Cl:9])=[CH:4][CH:3]=1)=[O:12]

Participants

3

Reactant 2

HCID 785HydroquinoneHCID 6577Chloroacetyl chloride

Product 1

HCID 222447benzene-1,4-diyl bis(chloroacetate)Yield 46%

Procedure

A mixture of hydroquinone (50 grams, 454.09 mmol) and chloroacetyl chloride (150 mL) was refluxed for 48 hours. Excess chloroacetyl chloride was distilled off, and the residue taken into ice water, filtered, dried, and recrystallised from ethyl acetate:hexane (1:6) to get pure product (55 grams, 46%) as a white fluffy powder. M.p: 127-128° C. 1H NMR (CDCl3) δ 4.20 (s, 25H, CH2), 7.24 (s, 2H, Ar).

Workup

  1. temperaturewas refluxed for 48 hours
  2. distillationExcess chloroacetyl chloride was distilled off
  3. filtrationfiltered
  4. customdried
  5. customrecrystallised from ethyl acetate:hexane (1:6)

Sources & evidence

ORD record
ord-28805a0cd17544e595f892c971c956f4
Source dataset
uspto-grants-2012_07
Patent number
US08217134B2

Reaction notes

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