Lithium hydroxide, monohydrate → 2-Isobutyl-succinic acid-4-t-butyl ester

HRID 458065Notes

Reaction equation

HRID 458065 reaction equation
C[O:2][C:3](=[O:17])[CH:4]([CH2:13][CH:14]([CH3:16])[CH3:15])[CH2:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].O[Li].O>CC(O)C.O>[C:9]([O:8][C:6](=[O:7])[CH2:5][CH:4]([CH2:13][CH:14]([CH3:15])[CH3:16])[C:3]([OH:17])=[O:2])([CH3:12])([CH3:11])[CH3:10]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 218883142-Isobutylsuccinic acid-4-t-butyl ester-1-methyl ester

Product 1

HCID 99427122-Isobutyl-succinic acid-4-t-butyl esterYield 77%

Reagents, catalysts & solvents 1

HCID 21889133Propan-2-ol--water (1/1)Solvent

Procedure

2-Isobutylsuccinic acid-4-t-butyl ester-1-methyl ester (11.1 g, 45.4 mmol) and LiOH.H2O (2.0 g, 47.7 mmol) are stirred in 180 mL of 3:1 IPA/H2O at room temperature overnight. The reaction mixture is extracted with Et2O (3×25 mL). The aqueous phase is acidified to pH=4, with saturated KH2PO4 and extracted with Et2O (3×50 mL). The Et2O is dried over MgSO4, and evaporated to give 8.0 g (77% yield) of 2-isobutyl-succinic acid-4-t-butyl ester as an oil. NMR (H1, 400 MHz, CDCl3) δ 0.9 (6H, m); δ 1.3 (1H, m); δ 1.4 (9H, s); δ 1.6 (2H, m); δ 2.3 (1H, dd); δ 2.6 (1H, dd); δ 2.8 (1H, m).

Workup

  1. extractionThe reaction mixture is extracted with Et2O (3×25 mL)
  2. extractionextracted with Et2O (3×50 mL)
  3. dry with materialThe Et2O is dried over MgSO4
  4. customevaporated

Sources & evidence

ORD record
ord-9ea1d9bf1fad4750962bc9e5f41fad60
Source dataset
uspto-grants-2007_03
Patent number
US07189747B2

Reaction notes

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