Dichloromethane → 1,2,4-Trimethyl-bicyclo[2.2.1]heptane-2-carboxylic acid methyl ester

HRID 61334Notes

Reaction equation

HRID 61334 reaction equation
[CH3:1][C:2]12[CH2:8][C:5]([CH3:9])([CH2:6][CH2:7]1)[CH2:4][C:3]2([CH3:13])[C:10]([OH:12])=[O:11].S(Cl)(Cl)=O.[CH2:18](Cl)Cl>>[CH3:18][O:11][C:10]([C:3]1([CH3:13])[CH2:4][C:5]2([CH3:9])[CH2:8][C:2]1([CH3:1])[CH2:7][CH2:6]2)=[O:12]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 24386Thionyl ChlorideHCID 89704987HCID 89704987, compound

Product 1

HCID 897054491,2,4-Trimethyl-bicyclo[2.2.1]heptane-2-carboxylic acid methyl esterYield 45%

Procedure

1,2,4-Trimethyl-bicyclo[2.2.1]heptane-2-carboxylic acid (obtained as detailed above) was dissolved in methylene chloride (50 mL), and added dropwise to thionyl chloride (100 mL) at 50° C. After 1 hour, excessive thionyl chloride was distilled out and methanol (100 mL) was added. The reaction mixture was stirred overnight and then poured into saturated aqueous sodium bicarbonate. The resulting mixture was extracted with toluene and the organic phase was distilled to provide 1,2,4-trimethyl-bicyclo[2.2.1]heptane-2-carboxylic acid methyl ester (65 g, 45% yield).

Workup

  1. distillationexcessive thionyl chloride was distilled out and methanol (100 mL)
  2. additionwas added
  3. additionpoured into saturated aqueous sodium bicarbonate
  4. extractionThe resulting mixture was extracted with toluene
  5. distillationthe organic phase was distilled

Sources & evidence

ORD record
ord-aed15a8e999946258e1c698aa591aacc
Source dataset
uspto-grants-2016_09
Patent number
US09441185B2

Reaction notes

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