Potassium Hydroxide → HCID 23075282, compound

HRID 2076445Notes

Reaction equation

HRID 2076445 reaction equation
[CH3:1][C:2]1([CH3:21])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([NH:12][C:13]([C:15]([O:17]C)=[O:16])=[O:14])[CH:10]=2)[C:5]([CH3:20])([CH3:19])[CH2:4][CH2:3]1.[OH-].[K+]>CO>[CH3:1][C:2]1([CH3:21])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([NH:12][C:13]([C:15]([OH:17])=[O:16])=[O:14])[CH:10]=2)[C:5]([CH3:20])([CH3:19])[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 58893582HCID 58893582, compound

Product 1

HCID 23075282HCID 23075282, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 25 mL round bottom flask equipped with a reflux condenser was charged with methyl (1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalen-7-ylcarbamoyl)formate 24 (0.200 g, 0.691 mmol), MeOH (10 mL) and KOH (0.078 g, 1.382 mmol). The reaction mixture was stirred for 3 h at reflux, evaporated to dryness and partitioned between EtOAc and H2O. 6N HCl was added to reach acidic pH and the organic layer was separated, washed with water, brine, dried with Na2SO4, filtered and concentrated on a rotary evaporator to give (1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalen-7-ylcarbamoyl)formic acid as a white solid 25 (0.157 g, 83% yield).

Workup

  1. customA 25 mL round bottom flask equipped with a reflux condenser
  2. temperatureat reflux
  3. customevaporated to dryness
  4. custompartitioned between EtOAc and H2O
  5. addition6N HCl was added
  6. customthe organic layer was separated
  7. washwashed with water, brine
  8. dry with materialdried with Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-6ac17480ce5a4669b2b2ea1fc67935cb
Source dataset
uspto-grants-2011_04
Patent number
US07923579B2

Reaction notes

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