Hydrochloric Acid → HCID 13912815, compound

HRID 615492Notes

Reaction equation

HRID 615492 reaction equation
[C:1]([C:4]1[CH:21]=[CH:20][C:7]([O:8][CH2:9][C:10]2[CH:19]=[CH:18][C:13]([C:14]([O:16]C)=[O:15])=[CH:12][CH:11]=2)=[C:6]([CH2:22][CH2:23][CH3:24])[C:5]=1[OH:25])(=[O:3])[CH3:2].O[Li].O.Cl>CO.O1CCCC1.O>[C:1]([C:4]1[CH:21]=[CH:20][C:7]([O:8][CH2:9][C:10]2[CH:19]=[CH:18][C:13]([C:14]([OH:16])=[O:15])=[CH:12][CH:11]=2)=[C:6]([CH2:22][CH2:23][CH3:24])[C:5]=1[OH:25])(=[O:3])[CH3:2]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 13912814HCID 13912814, compound

Product 1

HCID 13912815HCID 13912815, compoundYield 63.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 684 mg (2.0 mmoles) of methyl 4-(4-acetyl-3-hydroxy-2-propylphenoxy)methylbenzoate in 9 ml MeOH, 9 ml tetrahydrofuran and 3 ml water was treated with 420 mg (10 mmoles) LiOH.H2O and stirred at room temperature for 4 hours. The reaction mixture was diluted with water, acidified by addition of concentrated HCl and extracted with dichloromethane. The combined extracts were washed with water, dried with MgSO4 and evaporated to give a white solid. Recrystallization of this material from ether gave 416 mg (63% yield) of the title compound as fine white needles mp 188°-188.5° C.

Workup

  1. extractionextracted with dichloromethane
  2. washThe combined extracts were washed with water
  3. dry with materialdried with MgSO4
  4. customevaporated
  5. customto give a white solid
  6. customRecrystallization of this material from ether

Sources & evidence

ORD record
ord-cd7215f89de94801ab83b6c89975a047
Source dataset
uspto-grants-1985_02
Patent number
US04499299

Reaction notes

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