Hydrochloric Acid → 6-(2-Hydroxy-3,4,6-trimethylphenyl)hexanoic acid

HRID 1390561Notes

Reaction equation

HRID 1390561 reaction equation
[OH:1][C:2]1[C:16]([CH3:17])=[C:15]([CH3:18])[CH:14]=[C:13]([CH3:19])[C:3]=1[C:4]([CH2:6][CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11])=O.C1(C)C=CC=CC=1.Cl>O.[Zn]>[OH:1][C:2]1[C:16]([CH3:17])=[C:15]([CH3:18])[CH:14]=[C:13]([CH3:19])[C:3]=1[CH2:4][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11]

Participants

6

Reactant 3

HCID 313Hydrochloric Acid2×HCID 1140TolueneHCID 12906148HCID 12906148, compound

Product 1

HCID 129061366-(2-Hydroxy-3,4,6-trimethylphenyl)hexanoic acid

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 962WaterSolvent2×

Procedure

To 5-(2'-hydroxy-3',4',6'-trimethylbenzoyl)pentanoic acid (formula II-1 wherein R=H3C, X=H, Y=OH, n=4, in the free form) (0.262 part) were added water (16 volume parts), toluene (20 volume parts), concentrated hydrochloric acid (4 volume parts) and zinc amalgam prepared from 2 parts of zinc. The mixture was refluxed for 16 hours, during which time concentrated hydrochloric acid (6 volume parts) was added in three portions. After cooling, the reaction mixture was diluted with water and extracted with diethyl ether. The extract was washed with water and dried. The solvents were distilled off under reduced pressure to obtain 6-(2'-hydroxy-3',4',6'-trimethylphenyl)hexanoic acid (formula II-2 wherein R=H3C, X=H, Y=OH, n=4, in the free form)(0.251 part) as colorless needles melting at 96°-108° C.

Workup

  1. additionwas added in three portions
  2. temperatureAfter cooling
  3. extractionextracted with diethyl ether
  4. washThe extract was washed with water
  5. customdried
  6. distillationThe solvents were distilled off under reduced pressure

Sources & evidence

ORD record
ord-b4933d5e727c4341af3fc13217497ce0
Source dataset
uspto-grants-1979_02
Patent number
US04139545

Reaction notes

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