Acetic Acid → HCID 23338330, compound

HRID 262332Notes

Reaction equation

HRID 262332 reaction equation
C(OC([O:6][C:7]([CH3:22])([CH:20]=[CH2:21])[C:8]#[C:9][C:10]1(O)[C:15]([CH3:17])([CH3:16])[CH2:14][CH2:13][CH:12]=[C:11]1[CH3:18])C)C.[C:23]([OH:26])(=[O:25])[CH3:24]>CCCCCC>[CH3:18][C:11]1[CH:12]([O:26][C:23](=[O:25])[CH3:24])[CH2:13][CH2:14][C:15]([CH3:16])([CH3:17])[C:10]=1[C:9]#[C:8][C:7]([CH3:22])([OH:6])[CH:20]=[CH2:21]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 23338328HCID 23338328, compound

Product 1

HCID 23338330HCID 23338330, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

The compound 1-ethoxy-[1-(2,6,6-trimethyl-1-hydroxy-2-cyclohexen-1-yl)-3-methyl-4-penten-1-yn-3-oxy]ethane (9.5 g) in acetic acid (40 ml) was heated at 55° for 11/2 hr and then taken to dryness "in vacuo" (45° at 0.5 mmHg), dissolved in hexane, and chromatographed on silica gel (400 g). Elution with hexane-ether mixtures (4:1 parts vy volume and 3:1 parts by volume 500 ml cuts, 2 liters) yielded 1-(2,6,6-trimethyl-3-acetoxycyclohexen-1-yl)-3-methyl-4-penten-1-yn-3-ol (4.3 g) bp 165° (0.09 mmHg).

Workup

  1. customtaken to dryness "in vacuo" (45° at 0.5 mmHg)
  2. customchromatographed on silica gel (400 g)
  3. washElution with hexane-ether mixtures (4:1 parts vy volume and 3:1 parts by volume 500 ml cuts, 2 liters)

Sources & evidence

ORD record
ord-ffbb1e363eab4a58be7aab0da2ec11f2
Source dataset
uspto-grants-1979_05
Patent number
US04153805

Reaction notes

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