Peracetic Acid → Limonene oxide

HRID 649120

Reaction equation

HRID 649120 reaction equation
[CH3:1][C:2]1[CH2:7][CH2:6][C@@H:5]([C:8]([CH3:10])=[CH2:9])[CH2:4][CH:3]=1.C(=O)([O-])[O-:12].[Na+].[Na+].C(OO)(=O)C>>[CH3:9][C:8]([CH:5]1[CH2:6][CH:7]2[O:12][C:2]2([CH3:1])[CH2:3][CH2:4]1)=[CH2:10]

Participants

4

Reactant 3

HCID 6585Peracetic AcidHCID 10340Sodium CarbonateHCID 440917(+)-Limonene

Product 1

HCID 91496Limonene oxide

Procedure

A mechanically stirred mixture of 1 kg. (7.3 mol.) of d-limonene (7.3 mol.) and sodium carbonate (310.6 g) was cooled to 0°-10° C., and treated with 1.61 kg. (9.1 mol.) 40% peracetic acid by dropwise addition. After the addition was complete, the reaction mixture was stirred for another 45 min., washed with ice water, sodium carbonate, and brine. The oil was dried over magnesium sulfate, and distilled to give recovered limonene (30 g), the cis-epoxide (257 g) and trans-epoxide (296 g), and diepoxide (82 g).

Workup

  1. additionA mechanically stirred mixture of 1 kg
  2. additiontreated with 1.61 kg
  3. additionAfter the addition
  4. washwashed with ice water, sodium carbonate, and brine
  5. dry with materialThe oil was dried over magnesium sulfate
  6. distillationdistilled
  7. customto give
  8. customrecovered limonene (30 g)

Sources & evidence

ORD record
ord-2442665bc9f04580ae86d55c2770ba91
Source dataset
uspto-grants-1988_04
Patent number
US04738892

Linked notes

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