Acetic Acid → 2-(5-Acetoxyhept-1-yl)bicyclo[3.3.0]octan-7-one

HRID 1789549Notes

Reaction equation

HRID 1789549 reaction equation
[OH:1][CH:2]([CH2:16][CH3:17])[CH2:3][CH2:4][CH2:5][CH2:6][CH:7]1[CH2:14][CH2:13][CH:12]2[CH:8]1[CH2:9][C:10](=[O:15])[CH2:11]2.[C:18](O)(=[O:20])[CH3:19]>>[C:18]([O:1][CH:2]([CH2:16][CH3:17])[CH2:3][CH2:4][CH2:5][CH2:6][CH:7]1[CH2:14][CH2:13][CH:12]2[CH:8]1[CH2:9][C:10](=[O:15])[CH2:11]2)(=[O:20])[CH3:19]

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 15053004hexahydro-4-(5-hydroxyheptyl)-2(1H)-pentalenone3×

Product 1

HCID 142041172-(5-Acetoxyhept-1-yl)bicyclo[3.3.0]octan-7-one

Conditions

Temperature
70 °C

Procedure

The starting material from Example 3, 2-(5-hydroxyhept-1-yl)bicyclo[3.3.0]octan-7-one {hexahydro-4-(5-hydroxyheptyl)-2(1H)-pentalenone} (2.5 g, 10.5 mmoles) is diluted with glacial acetic acid (10 ml) and stirred in a 70° C. water bath for 4 hours. The reaction is cooled to room temperature and partitioned between ether (50 ml) and water (50 ml). The ether layer is separated and the aqueous phase extracted with ether (2×50 ml). The organic layers are combined, neutralized with a solution of saturated sodium bicarbonate, and dried over anhydrous sodium sulfate. The solvent is removed under vacuum leaving a clear yellow oil. The crude product is chromatographed on silica gel and subsequently kugelrohred under vacuum leaving a clear, colorless oil (2.1 g, 7.4 mmoles).

Workup

  1. temperatureThe reaction is cooled to room temperature
  2. custompartitioned between ether (50 ml) and water (50 ml)
  3. customThe ether layer is separated
  4. extractionthe aqueous phase extracted with ether (2×50 ml)
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent is removed under vacuum
  7. customleaving a clear yellow oil
  8. customThe crude product is chromatographed on silica gel

Sources & evidence

ORD record
ord-3dd62530494549a98c1c58849b00b4ae
Source dataset
uspto-grants-1987_08
Patent number
US04689345

Reaction notes

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