Ethylene Glycol → 5-Methoxy-3-phenyl-1,2,3,4-tetrahydro-1-naphthalene carboxylic acid

HRID 982124Notes

Reaction equation

HRID 982124 reaction equation
C(C1[C:12]2[C:7](=[C:8]([O:13][CH3:14])[CH:9]=[CH:10][CH:11]=2)[CH2:6][CH:5]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:4]1)#N.[OH-:21].[K+].Cl.[CH2:24]([OH:27])[CH2:25]O>>[CH3:14][O:13][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:7]=1[CH2:6][CH:5]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:4][CH:25]2[C:24]([OH:27])=[O:21]

Participants

5

Reactant 4

HCID 174Ethylene GlycolHCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 200690891-Cyano-5-methoxy-3-phenyl-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 200690375-Methoxy-3-phenyl-1,2,3,4-tetrahydro-1-naphthalene carboxylic acid

Conditions

Temperature
-20 °C

Procedure

A mixture of 5.03 g (19.1 mmol) of 1-cyano-5-methoxy-3-phenyl-1,2,3,4-tetrahydronaphthalene, from Step 2, 40 mL of 5% aqueous potassium hydroxide solution and 90 mL of ethylene glycol is heated at reflux temperature for 8 h. The reaction mixture is then cooled to -20° C. and made acidic by the addition of cold concentrated aqueous hydrochloric acid solution. The acidic solution is extracted with methylene chloride and the organic extracts are washed with brine, dried over anhydrous magnesium sulfate, filtered and evaporated to give the title compound which is used in the next step without purification.

Workup

  1. temperatureat reflux temperature for 8 h
  2. extractionThe acidic solution is extracted with methylene chloride
  3. washthe organic extracts are washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-fc91d22e97bb4fbd813fd6436c68419a
Source dataset
uspto-grants-1991_02
Patent number
US04994486

Reaction notes

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