Benzyl Alcohol → Benzylsuccinic acid

HRID 1459156Notes

Reaction equation

[C:1]([OH:8])(=[O:7])[CH2:2][CH2:3][C:4]([OH:6])=[O:5].[CH2:9](O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C1CCC(N=C=NC2CCCCC2)CC1>>[CH2:9]([CH:3]([CH2:2][C:1]([OH:8])=[O:7])[C:4]([OH:6])=[O:5])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

Reactant 3

HCID 244Benzyl Alcohol

HCID 1110Succinic Acid

HCID 10868Dicyclohexylcarbodiimide

Product 1

HCID 3858Benzylsuccinic acid

Procedure

Succinic acid can be protected with benzyl alcohol in the presence of DCC to obtain mono benzyl succinic acid. The product can then be purified via silica gel chromatography. Mono benzyl succinic acid can then be activated with HOSU in the presence of DCC and then coupled to Tris to obtain benzyl-succinate. This compound can then be acylated with lauric acid in the presence of DCC to give a mixture of the title compound. The three compounds can then be separated by silica gel chromatography with elution by organic solvents.

Sources & evidence

ORD record: ord-ecb09c51722b4650b64dbd4c1e978c2a
Source dataset: uspto-grants-1998_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05854224

Reaction notes

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