Sodium Hydroxide → HCID 11974934, compound

HRID 363053Notes

Reaction equation

HRID 363053 reaction equation
[OH-].[Na+].[CH:3]1([CH2:9][O:10][C:11]2[CH:12]=[C:13]([CH2:17][C:18]([O:20]CC)=[O:19])[CH:14]=[CH:15][CH:16]=2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1>C(O)(C)(C)C.O.C(OCC)(=O)C>[CH:3]1([CH2:9][O:10][C:11]2[CH:12]=[C:13]([CH2:17][C:18]([OH:20])=[O:19])[CH:14]=[CH:15][CH:16]=2)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 53884698HCID 53884698, compound

Product 1

HCID 11974934HCID 11974934, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6386tert-ButanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
23 °C

Procedure

A solution of aqueous sodium hydroxide (1N, 14 mL, 14.0 mmol, 10 equiv) was added to a solution of ethyl 3-cyclohexylmethyloxy-phenylacetate 29-3 (384 mg, 1.39 mmol, 1 equiv) in a mixture of t-butanol (8 mL) and water (4 mL) at 23° C. The reaction mixture was heated at reflux for 2 h. The solution was cooled to 23° C. and was diluted with ethyl acetate (50 mL). The organic layer was washed with an aqueous 10% potassium hydrogen sulfate solution (2×25 mL), then was dried over magnesium sulfate and was concentrated to afford the product 29-4 as a white solid, which was used without further purification.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 2 h
  3. washThe organic layer was washed with an aqueous 10% potassium hydrogen sulfate solution (2×25 mL)
  4. dry with materialwas dried over magnesium sulfate
  5. concentrationwas concentrated

Sources & evidence

ORD record
ord-f20e2f42afa64f1399f2405ec9718f25
Source dataset
uspto-grants-1999_02
Patent number
US05872138

Reaction notes

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