Methanol → Tricyclo(3.3.1.13,7)decane-1-carboxylic acid, methyl ester

HRID 866544Notes

Reaction equation

HRID 866544 reaction equation
[C:1]12([C:11]([OH:13])=[O:12])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[CH3:14]O.OS(O)(=O)=O>O>[CH3:14][O:12][C:11]([C:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2)=[O:13]

Participants

5

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 132351-Adamantanecarboxylic acid

Product 1

HCID 136553Tricyclo(3.3.1.13,7)decane-1-carboxylic acid, methyl esterYield 77.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1-adamantanecarboxylic acid (572 gm.), methanol (2.2 liters), and H2SO4 (90 ml.) was refluxed 5 hours and then cooled to room temperature overnight. The reaction mixture was poured into 28 liters of water and extracted with chloroform (2 × 150 ml.) for each 3.5 liters of solution). The chloroform extracts were combined, washed with water, dried, and concentrated. The residual oil was distilled to give 476 gm. product (77.5% yield) b17 approx. 143°.

Workup

  1. temperaturewas refluxed 5 hours
  2. extractionextracted with chloroform (2 × 150 ml.) for each 3.5 liters of solution)
  3. washwashed with water
  4. customdried
  5. concentrationconcentrated
  6. distillationThe residual oil was distilled
  7. customto give 476 gm

Sources & evidence

ORD record
ord-bfe288784b3a45c7a0c682747a6addeb
Source dataset
uspto-grants-1978_07
Patent number
US04100170

Reaction notes

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