Hydrochloric Acid → HCID 20428672, compound

HRID 615496Notes

Reaction equation

HRID 615496 reaction equation
[C:1]([C:4]1[CH:21]=[C:20]([I:22])[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]([CH2:23][CH2:24][CH3:25])[C:5]=1[OH:26])(=[O:3])[CH3:2].O[Li].O.CO.Cl>O1CCCC1.O>[C:1]([C:4]1[CH:21]=[C:20]([I:22])[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]([CH2:23][CH2:24][CH3:25])[C:5]=1[OH:26])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 20428667HCID 20428667, compound

Product 1

HCID 20428672HCID 20428672, compoundYield 91.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
22 °C

Procedure

A solution of 245 mg (0.523 mmoles) of methyl 4(-4-acetyl-3-hydroxy-6-iodo-2-propylphenoxy)methylbenzoate in 3 ml of tetrahydrofuran and 0.8 ml of water was treated with 110 mg (2.62 mmoles) of LiOH.H2O and stirred at 22° C. for one hour. The temperature was brought to 55° C. and 3 ml of MeOH was added after 2 hours of reaction. After a total reaction time of 31/2 hours, the mixture was allowed to cool, diluted with water, acidified by addition of concentrated HCl and extracted with dichloromethane. The combined extracts were washed with water, dried over MgSO4 and evaporated to give 217 mg of white powder mp 167°-168.5° C.

Workup

  1. customwas brought to 55° C.
  2. temperatureto cool
  3. extractionextracted with dichloromethane
  4. washThe combined extracts were washed with water
  5. dry with materialdried over MgSO4
  6. customevaporated

Sources & evidence

ORD record
ord-b177efc150ae4035baa9dc2cec974d8f
Source dataset
uspto-grants-1985_02
Patent number
US04499299

Reaction notes

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