Acetic Acid → 4-(4-Hydroxy-3,5-dimethylphenyl)butanoic acid

HRID 980756

Reaction equation

HRID 980756 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:11](=O)[CH2:12][CH2:13][C:14]([OH:16])=[O:15])[CH:5]=[C:6]([CH3:10])[C:7]=1[O:8]C.C(O)(=O)C.Cl>O>[CH3:1][C:2]1[CH:3]=[C:4]([CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])[CH:5]=[C:6]([CH3:10])[C:7]=1[OH:8]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 140320874-(3,5-Dimethyl-4-methoxyphenyl)-4-oxobutyric acid

Product 1

HCID 143485904-(4-Hydroxy-3,5-dimethylphenyl)butanoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-(3,5-dimethyl-4-methoxyphenyl)-4-oxobutyric acid (13 g), zinc amalgam [prepared from zinc (15 g) and mercuric chloride (1.5 g)], glacial acetic acid (70 ml), water (70 ml) and concentrated hydrochloric acid (170 ml) was heated at reflux for 12 hr. The cooled mixture was filtered and the filtrate was poured into water (1 liter). The mixture was extracted with ethyl acetate and the organic fraction was washed four times with water. The dried (MgSO4) organic fraction was evaporated to give 4-(3,5-dimethyl-4-hydroxyphenyl)butyric acid as a pale yellow oil. Pmr spectrum (CDCl3 ; δ in ppm): 1.79-2.64 (6H,m); 2.22 (6H,s); 6.79 (2H,s); 7.6 (2H,brs).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 12 hr
  3. filtrationThe cooled mixture was filtered
  4. additionthe filtrate was poured into water (1 liter)
  5. extractionThe mixture was extracted with ethyl acetate
  6. washthe organic fraction was washed four times with water
  7. dry with materialThe dried (MgSO4) organic fraction
  8. customwas evaporated

Sources & evidence

ORD record
ord-a299a93302ba48d8943b2b76f6408986
Source dataset
uspto-grants-1987_01
Patent number
US04639267

Linked notes

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