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

HRID 1039434Notes

Reaction equation

HRID 1039434 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-0dd668ee14e541dea90d47c4b142d01c
Source dataset
uspto-grants-2013_10
Patent number
US08552139B2

Reaction notes

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