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

HRID 2403065Notes

Reaction equation

HRID 2403065 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-d913ab81f294448685415952b29e2661
Source dataset
uspto-grants-2014_08
Patent number
US08802147B2

Reaction notes

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