Water → HCID 21997001, compound

HRID 1978209Notes

Reaction equation

HRID 1978209 reaction equation
[CH3:1][C:2]1([CH3:14])[CH2:10][CH2:9][CH:8]2[C:11](=[CH2:12])[CH:3]1[CH2:4][CH2:5][CH:6]([OH:13])[CH2:7]2.[C:15](OC(=O)C)(=[O:17])[CH3:16].O>P(=O)(O)(O)O.CCOCC>[C:15]([O:13][CH:6]1[CH2:5][CH2:4][CH:3]2[C:11](=[CH2:12])[CH:8]([CH2:9][CH2:10][C:2]2([CH3:14])[CH3:1])[CH2:7]1)(=[O:17])[CH3:16]

Participants

6

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 21996999HCID 21996999, compound

Product 1

HCID 21997001HCID 21997001, compound

Reagents, catalysts & solvents 2

HCID 1004Phosphoric AcidCatalystHCID 3283Diethyl EtherSolvent

Procedure

In a 3-necked flask which was equipped with a reflux condenser, there were placed, under N2-atmosphere, 0.9 g (4.6 mmoles) of 7,7-dimethyl-10-methylene-bicyclo[4.3.1]decan-3-ol, 8 ml of acetic anhydride and 1 drop of phosphoric acid. The reaction mixture was stirred overnight at room temperature. Then 50 ml of H2O were added and the solution stirred one more night at room temperature. The resulting mixture was taken up in ether, washed to neutrality with brine and dried over Na2SO4. After filtration and concentration in vacuo, the product was distilled in a bulb-to-bulb apparatus at 150° C. (10 Pa). There were obtained 1.09 g of a colorless oil in 99% of the theoretical yield. The thus-obtained mixture was composed of 2 isomers (71/29) which were separated by gas chromatography on a chemically inert CARBOWAX® column having a length of 5 meters.

Workup

  1. customIn a 3-necked flask which was equipped with a reflux condenser
  2. stirringthe solution stirred one more night at room temperature
  3. washwashed
  4. dry with materialdried over Na2SO4
  5. filtrationAfter filtration and concentration in vacuo
  6. distillationthe product was distilled in a bulb-to-bulb apparatus at 150° C. (10 Pa)

Sources & evidence

ORD record
ord-05058f5449a14e5ab0b6c268b7535e48
Source dataset
uspto-grants-2001_05
Patent number
US06235926B1

Reaction notes

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