Acrylic Acid → 1-Oxaspiro(4.5)decan-2-one, 8-(1-methylethyl)-, trans-

HRID 463493Notes

Reaction equation

HRID 463493 reaction equation
[CH:1]([CH:4]1[CH2:9][CH2:8][CH:7]([OH:10])[CH2:6][CH2:5]1)([CH3:3])[CH3:2].[C:11](O)(=[O:14])[CH:12]=[CH2:13].C(OOC(C)(C)C)(C)(C)C>>[CH:1]([CH:4]1[CH2:9][CH2:8][C:7]2([O:10][C:11](=[O:14])[CH2:12][CH2:13]2)[CH2:6][CH2:5]1)([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 6581Acrylic AcidHCID 8033Di-tert-butyl peroxideHCID 207394-Isopropylcyclohexanol2×

Product 1

HCID 64520491-Oxaspiro(4.5)decan-2-one, 8-(1-methylethyl)-, trans-

Procedure

To 1247 g of 4-isopropylcyclohexanol at 143°-150° C. was added in 6 hrs a mixture of 71.1 g (1.0 m) acrylic acid, 142 g (1.0 m) 4-isopropylcyclohexanol and 14.6 g (0.1 m) di-tert-butylperoxide. After an additional hour at 143°-150° the mixture was distilled at reduced pressure yielding 142.1 g. Bp:125°-141° C. (1.0 mm Hg). Odor:woody, milky-lactone, dry. Analysis:99% pure by VPC: 44% cis (odor:nonalactone, celery-lactone) 56% trans (odor:strong woody, cinnamic, urine)

Workup

  1. distillationAfter an additional hour at 143°-150° the mixture was distilled at reduced pressure
  2. customyielding 142.1 g
  3. dry with materialOdor:woody, milky-lactone, dry

Sources & evidence

ORD record
ord-e0902b9c68e4461bb1a49707bfb1348d
Source dataset
uspto-grants-1985_05
Patent number
US04519944

Reaction notes

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