4-Hydroxyphenylglyoxal → HCID 53965414, compound

HRID 893433Notes

Reaction equation

HRID 893433 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH:10]=[O:11])=O)=[CH:4][CH:3]=1>[Pd].CO>[CH3:6][CH:5]([CH3:8])[CH2:4][CH2:3][O:11][CH2:10][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][CH:4]=1

Participants

4

Reactant 1

HCID 905684-Hydroxyphenylglyoxal

Product 1

HCID 53965414HCID 53965414, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

An autoclave was charged with isoamyl acetal of p-hydroxyphenylglyoxal (20 g, 65 mmol), palladium catalyst (2 g, 10% Pd/C 2 mmol) and methanol (150 ml, 5% HCl). After purging with nitrogen, the autoclave was pressured to 50 psig with hydrogen. After three (3) hours, the pressure dropped to 15 psig. The reaction was then recharged with hydrogen to 50 psig for one (1) hour. Then, it was further charged with hydrogen to 200 psig and was allowed to carry out the reaction overnight at 40° C. Analysis indicated a 40% yield of the product 4-2[2'(3''-methylbutoxy)ethyl]phenol, identified by MS m/z 208 (M+), 165, 137.

Workup

  1. customAfter purging with nitrogen
  2. additionAfter three (3) hours, the pressure dropped to 15 psig
  3. additionThen, it was further charged with hydrogen to 200 psig
  4. customthe reaction overnight at 40° C

Sources & evidence

ORD record
ord-98b254da3b65401781af1ff7e42a715e
Source dataset
uspto-grants-1992_06
Patent number
US05124489

Reaction notes

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