Benzyl Alcohol → 2,2-Dimethyl-4-benzyloxycarbonylbutyric acid

HRID 964193

Reaction equation

HRID 964193 reaction equation
[CH3:1][C:2]1([CH3:10])[CH2:8][CH2:7][C:6](=[O:9])[O:5][C:3]1=[O:4].[CH2:11]([OH:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CC(C)(CCC(O)=O)C(O)=O.OS(O)(=O)=O>C(Cl)Cl.CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[CH3:1][C:2]([CH3:10])([CH2:8][CH2:7][C:6]([O:18][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])[C:3]([OH:5])=[O:4]

Participants

8

Reactant 4

HCID 244Benzyl AlcoholHCID 1118Sulfuric AcidHCID 126812,2-Dimethylglutaric acidHCID 76247Dihydro-3,3-dimethyl-2H-pyran-2,6(3H)-dione

Product 1

HCID 190800452,2-Dimethyl-4-benzyloxycarbonylbutyric acidYield 73.6%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 3 g (0.021 mol) of 2.2-dimethylglutaric anhydride, 2.0 ml (0.019 mol) of benzyl alcohol in 10 ml of CH2Cl2 was added 100 mg of DMAP and 3.4 ml of pyridine. The resulting solution was stired at room temperature for 4 h. After additional 2.2-dimethyl-glutaric acid (0.7 g, 4.9 mmol) was added, the mixture continued to be stirred overnight, then poured into 0.5M H2SO4 (aq.) solution and extracted with CH2Cl2. The organic layer was washed with brine, dried over Na2SO4 and filtered. Concentration followed by purification by flash chromatography on silica gel using EtOAc/hexane (1:1) as the irrigant gave 3.5 g of desired product in 66% yield and 1.2 g of isomer in 23% yield.

Workup

  1. extractionextracted with CH2Cl2
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationConcentration
  6. customfollowed by purification by flash chromatography on silica gel

Sources & evidence

ORD record
ord-42e4ecca3cde4cb382cfced4daddbcd4
Source dataset
uspto-grants-1998_06
Patent number
US05767256

Linked notes

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