Hydrochloric Acid → HCID 10067333, compound

HRID 2112015Notes

Reaction equation

HRID 2112015 reaction equation
CS([O:5][C:6]1[CH:32]=[CH:31][C:9]([O:10][CH2:11][CH2:12][C:13]2[CH:14]=[C:15]([CH:28]=[CH:29][CH:30]=2)[O:16][CH2:17][C:18]2[CH:27]=[CH:26][CH:25]=[CH:24][C:19]=2[C:20]([O:22]C)=[O:21])=[CH:8][CH:7]=1)(=O)=O.[OH-].[Li+].Cl>C1COCC1.O>[OH:5][C:6]1[CH:7]=[CH:8][C:9]([O:10][CH2:11][CH2:12][C:13]2[CH:14]=[C:15]([CH:28]=[CH:29][CH:30]=2)[O:16][CH2:17][C:18]2[CH:27]=[CH:26][CH:25]=[CH:24][C:19]=2[C:20]([OH:22])=[O:21])=[CH:31][CH:32]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 86601925HCID 86601925, compound

Product 1

HCID 10067333HCID 10067333, compoundYield 18.3%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

Methyl 2-{[3-(2-{4-[(methylsulfonyl)oxy]phenoxy}ethyl)phenoxy]methyl}benzoate (0.109 g, 0.24 mmol) was dissolved in a mixture of THF/water (7/1, 2.5 ml). Lithium hydroxide (23 mg, 0.96 mmol) was added. The reaction was performed in a single node microwave oven (7 min, 150° C.). The mixture was acidified (HCl, 1 ml, 1 M) and the water phase was extracted with two portions of EtOAc. The organic phases were combined, dried (MgSO4) and the solvent was removed by evaporation and gave 16 mg of 2-({3-[2-(4-hydroxyphenoxy)ethyl]phenoxy}methyl)benzoic acid (yield 18%)

Workup

  1. customThe reaction was performed in a single node microwave oven
  2. custom(7 min, 150° C.)
  3. extractionthe water phase was extracted with two portions of EtOAc
  4. dry with materialdried (MgSO4)
  5. customthe solvent was removed by evaporation

Sources & evidence

ORD record
ord-9518b94ce06e44d38b30bda5676dc505
Source dataset
uspto-grants-2009_04
Patent number
US07521461B2

Reaction notes

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