Water → 4-(3-Methoxyphenyl)-3,3-dimethylbutanoic acid

HRID 1274162Notes

Reaction equation

HRID 1274162 reaction equation
C([CH:3]([C:9]([CH3:20])([CH3:19])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=1)[C:4]([O:6]CC)=[O:5])#N.[OH-].[K+].O>C=C>[CH3:19][C:9]([CH3:20])([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=1)[CH2:3][C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 22120417Ethyl 2-cyano-3,3-dimethyl-4-(3-methoxyphenyl)butanoate

Product 1

HCID 221204124-(3-Methoxyphenyl)-3,3-dimethylbutanoic acidYield 90.9%

Reagents, catalysts & solvents 1

HCID 6325EthyleneSolvent

Procedure

A solution of ethyl 2-cyano-3,3-dimethyl-4-(3-methoxyphenyl)butanoate (9.0 g, 0.033 mol) and KOH (9.2 g, 0.163 mol) in ethylene gylcol (100 mL) was heated at 180° C. for 2 days. The solution was cooled to room temperature, poured into water (200 mL) and extracted with ether (100 mL). The organic layer was separated, dried (MgSO4) and evaporated to afford the acid (6.7 g, 0.03 mol)as brown oil, which was used without further purification. 1H NMR (360 MHz, CDCl3) δ 1.06 (6H, s), 2.24 (2H, s), 2.66 (2H, s), 3.81 (3H, s), 6.74-6.79 (3H, m), 7.19 (1H, t, J=8.1 Hz). MS (ES+) 223 (M+1).

Workup

  1. extractionextracted with ether (100 mL)
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-7a78b9be9a2842d08d03c6f835c27800
Source dataset
uspto-grants-2000_12
Patent number
US06156761

Reaction notes

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