tert-Butyl methyl ether → 1,2-Benzenediol, 4-(3-hydroxypropyl)-

HRID 909697

Reaction equation

HRID 909697 reaction equation
O[CH2:2][C:3]([C:5]1[CH:6]=[C:7]([OH:12])[C:8](=[CH:10][CH:11]=1)[OH:9])=O.[CH3:13][O:14]C(C)(C)C>>[CH:11]1[C:5]([CH2:3][CH2:2][CH2:13][OH:14])=[CH:6][C:7]([OH:12])=[C:8]([OH:9])[CH:10]=1

Participants

3

Reactant 2

HCID 15413tert-Butyl methyl etherHCID 221344442-Hydroxy-3′,4′-dihydroxyacetophenone

Product 1

HCID 112174641,2-Benzenediol, 4-(3-hydroxypropyl)-

Conditions

Temperature
40 °C

Procedure

A special house made pressure reactor, a 50 ml 10 bar glass reactor with steel mantle and a magnetic stirring bar, was charged with catalyst, 4-hydroxyacetyl-catechol (produced according to Example 2) and t-butyl methyl ether. The reactor was evacuated and filled with hydrogen. Hydrogenation was started by stirring at 5 bar hydrogen pressure while heating to 40° C. By the end of the reaction the hydrogen was replaced by air, the slurry was filtered, the catalyst was washed with ethyl acetate. After evaporation of the solvents and drying at 1 mbar the product was analyzed quantitatively. The details of some reactions and the results are shown in Table 1.

Workup

  1. customThe reactor was evacuated
  2. additionfilled with hydrogen
  3. customBy the end of the reaction the hydrogen
  4. filtrationthe slurry was filtered
  5. washthe catalyst was washed with ethyl acetate
  6. customAfter evaporation of the solvents
  7. customdrying at 1 mbar the product

Sources & evidence

ORD record
ord-3c54dba0bde4486c8305ae18deb44e6c
Source dataset
uspto-grants-2011_09
Patent number
US08017815B2

Linked notes

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