2-Methoxyethanol → 2-(4-Benzyloxybenzyl)-5-phenylvaleric acid

HRID 1871654Notes

Reaction equation

HRID 1871654 reaction equation
[OH-].[K+].[CH2:3]([O:10][C:11]1[CH:37]=[CH:36][C:14]([CH2:15][C:16]([CH2:27][CH2:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)(C(OCC)=O)[C:17]([O:19]CC)=[O:18])=[CH:13][CH:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.COCCO>O>[CH2:3]([O:10][C:11]1[CH:37]=[CH:36][C:14]([CH2:15][CH:16]([CH2:27][CH2:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:17]([OH:19])=[O:18])=[CH:13][CH:12]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 80192-MethoxyethanolHCID 14797Potassium HydroxideHCID 18625695Diethyl 2-(4-benzyloxybenzyl)-2-(3-phenylpropyl)malonate

Product 1

HCID 186257682-(4-Benzyloxybenzyl)-5-phenylvaleric acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

2.00 g of potassium hydroxide was added to a mixture of 3.91 g of diethyl 2-(4-benzyloxybenzyl)-2-(3-phenylpropyl)malonate obtained in Reference example 12(a), 30 ml of 2-methoxyethanol and 3 ml of water, and the resulting mixture was stirred on an oil bath of 130° C. for 1.5 hours. After the reaction, the reaction mixture was concentrated, water and ethyl acetate were added to the concentrated mixture, and then 6N hydrochloric acid was added thereto to make it acidic. Then, the ethyl acetate layer was separated, washed with an aqueous NaCl solution and dried over anhydrous magnesium sulfate, followed by concentration. The residual syrup was dissolved in 20 ml of xylene, and the mixture was stirred for one hour and concentrated. The syrup-like 2-(4-benzyloxybenzyl)-5-phenylvaleric acid thus obtained was dissolved in 40 ml of ethanol, and 1 ml of conc. sulfuric acid was added thereto. The resulting mixture was stirred at 80° C. for 3 hours and allowed to stand at room temperature for 16 hours. The reaction mixture was concentrated, and the residue was dissolved in ethyl acetate and water, followed by separation of the ethyl acetate layer. The extract thus obtained was dried over anhydrous magnesium sulfate and concentrated to obtain 3.32 g of the desired compound as a syrup.

Workup

  1. customAfter the reaction
  2. concentrationthe reaction mixture was concentrated
  3. additionwater and ethyl acetate were added to the concentrated mixture
  4. addition6N hydrochloric acid was added
  5. customThen, the ethyl acetate layer was separated
  6. washwashed with an aqueous NaCl solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationfollowed by concentration
  9. dissolutionThe residual syrup was dissolved in 20 ml of xylene
  10. stirringthe mixture was stirred for one hour
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-3a6f4dc352e64ccbad9cd432e6f6b06c
Source dataset
uspto-grants-2000_08
Patent number
US06103907

Reaction notes

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