Hydroquinone → 2,5-Di-tert-butylhydroquinone

HRID 1004498

Reaction equation

HRID 1004498 reaction equation
[C:1]1([CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[OH:2].[CH3:9][C:10](OC)([CH3:12])[CH3:11].[C:15]1(S(O)(=O)=O)[CH:20]=[CH:19]C=CC=1.[CH3:25]CCCCC>>[C:10]([C:3]1[CH:4]=[C:5]([OH:6])[C:7]([C:20]([CH3:19])([CH3:15])[CH3:25])=[CH:8][C:1]=1[OH:2])([CH3:12])([CH3:11])[CH3:9]

Participants

5

Reactant 4

HCID 785HydroquinoneHCID 7371Benzenesulfonic AcidHCID 8058HexaneHCID 15413tert-Butyl methyl ether

Product 1

HCID 23742,5-Di-tert-butylhydroquinoneYield 58.3%

Conditions

Temperature
20 °C

Procedure

12.4 g (0.113 mol) of hydroquinone, 49.8 g of MTBE (0.566 mol, 5 eq.) and 21.5 g (0.113 mol, 1 eq.) of 85% benzenesulphonic acid are introduced, under a stream of nitrogen, into a 250 ml reactor. The medium is then brought to 60° C. After maintaining these conditions for 5 hours, 25 ml of hexane are added and the reaction medium is cooled to 20° C. and then filtered in order to obtain 17.8 g of wet cake. This filter cake is placed in an oven (35° C.) under maximum vacuum for 12 h to give 14.6 g (58.3% yield for an 80% degree of conversion) of 2,5-di-tert-butylhydroquinone.

Workup

  1. customis then brought to 60° C
  2. temperatureAfter maintaining these conditions for 5 hours
  3. filtrationfiltered in order
  4. customto obtain 17.8 g of wet cake
  5. customThis filter cake is placed in an oven

Sources & evidence

ORD record
ord-bf89a97b7a574a288dab03302489a064
Source dataset
uspto-grants-2000_04
Patent number
US06049015

Linked notes

Loading…