Ethylene Glycol → HCID 54424481, compound

HRID 2073382Notes

Reaction equation

HRID 2073382 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([OH:12])=[CH:9]2)=[CH:4][CH:3]=1.[C:13]([OH:17])(=[O:16])[CH2:14]S.[OH-].[Na+].C(O)CO>O>[OH:12][C:8]1[CH:7]=[CH:6][C:5]2[C:10](=[CH:11][C:2]([CH3:1])=[CH:3][CH:4]=2)[C:9]=1[CH2:14][C:13]([OH:17])=[O:16]

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 1133Thioglycolic AcidHCID 14798Sodium HydroxideHCID 2591907-methylnaphthalen-2-ol

Product 1

HCID 54424481HCID 54424481, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 7-methylnaphth-2-ol (5 g), thioglycolic acid (3 g), sodium hydroxide (2 g) and ethylene glycol (10 ml) was stirred at 145° under an atmosphere of argon for 20 h. The mixture was cooled, water (100 ml) was added, and the mixture was heated at 90° for 2 h. The mixture was then washed with ethyl acetate and the aqueous phase was separated, acidified with concentrated hydrochloric acid, and extracted twice with ethyl acetate. The ethyl acetate extracts were combined, dried and evaporated to dryness under reduced pressure, and the residue was triturated with toluene. The insoluble solid thus produced was filtered off, washed with toluene and dried to give 2-hydroxy-7-methyl-1-naphthylacetic acid, m.p. 138°-140°.

Workup

  1. temperatureThe mixture was cooled
  2. temperaturethe mixture was heated at 90° for 2 h
  3. washThe mixture was then washed with ethyl acetate
  4. customthe aqueous phase was separated
  5. extractionextracted twice with ethyl acetate
  6. customdried
  7. customevaporated to dryness under reduced pressure
  8. customthe residue was triturated with toluene
  9. customThe insoluble solid thus produced
  10. filtrationwas filtered off
  11. washwashed with toluene
  12. customdried

Sources & evidence

ORD record
ord-24e363dd5b674808ad6d3b8cb2330afd
Source dataset
uspto-grants-1990_04
Patent number
US04916148

Reaction notes

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