Acetic Acid → HCID 58999579, compound

HRID 1593587Notes

Reaction equation

HRID 1593587 reaction equation
[CH3:1][C:2]12[CH2:12][C:6]3([CH3:13])[CH2:7][C:8]([CH3:11])([CH2:10][C:4](C(O)=O)([CH2:5]3)[CH2:3]1)[CH2:9]2.[C:17]([OH:20])(=O)[CH3:18].S(Cl)([Cl:23])=O>CO.CCOC(C)=O.[Pd]>[CH3:1][C:2]12[CH2:12][C:6]3([CH3:13])[CH2:7][C:8]([CH3:11])([CH2:10][C:4]([CH2:18][C:17]([Cl:23])=[O:20])([CH2:5]3)[CH2:3]1)[CH2:9]2

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 24386Thionyl ChlorideHCID 28022683,5,7-trimethyladamantane-1-carboxylic acid

Product 1

HCID 58999579HCID 58999579, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

3,5,7-trimethyl adamantane-1-carboxylic acid was converted to it's acid chloride per the procedure described for 3,5-dimethyl-adamantan-1-yl)-acetic acid. It was then homologated to the corresponding benzyl ester via the procedure described in Tetrahedron Letters, 1980, 21, 4461-4462. The benzyl ester was converted to the acid by standard hydrogenation conditions of 10% Pd/C in MeOH/EtOAc::1:1. The acid was then converted to the acid chloride via standard treatment with thionyl chloride at reflux for 1 to 2 hours. Excess reagent was azeotropically removed with hexanes and the resulting acid chloride was used without further purification.

Workup

  1. temperatureat reflux for 1 to 2 hours
  2. customExcess reagent was azeotropically removed with hexanes
  3. customthe resulting acid chloride was used without further purification

Sources & evidence

ORD record
ord-fdeaea5d1a574e0ea697ad8ca4fad248
Source dataset
uspto-grants-2007_11
Patent number
US07297700B2

Reaction notes

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