Allyl Alcohol → 4-(Allyloxy)-4-oxobutanoic acid

HRID 1643428Notes

Reaction equation

HRID 1643428 reaction equation
[CH2:1]([OH:4])[CH:2]=[CH2:3].C(N(CC)CC)C.[C:12]1(=[O:18])[O:17][C:15](=[O:16])[CH2:14][CH2:13]1>ClCCl>[CH2:1]([O:4][C:12](=[O:18])[CH2:13][CH2:14][C:15]([OH:17])=[O:16])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 7858Allyl AlcoholHCID 7922Succinic anhydrideHCID 8471Triethylamine

Product 1

HCID 22017124-(Allyloxy)-4-oxobutanoic acidYield 82.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of allyl alcohol (2.27 g, 39.0 mmol) in dichloromethane (60 ml), triethylamine (6.27 ml, 4.55 mmol) was added, then succinic anhydride (3.00 g, 30.0 mmol) was slowly added; the mixture was stirred at rt overnight. Then the mixture was diluted in dichloromethane and washed with 5% solution of NaH2PO4 (2×80 mL). The organic layer was dried over sodium sulfate, filtered and evaporated in vacuo, affording 3.90 g of desired product as a colourless oil.

Workup

  1. washwashed with 5% solution of NaH2PO4 (2×80 mL)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-7dc5251c93b745619cb42ed2aeac695f
Source dataset
uspto-grants-2012_02
Patent number
US08119806B2

Reaction notes

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