Hydrogen Peroxide → HCID 59289018, compound

HRID 386331Notes

Reaction equation

[CH2:1]([CH:6]1[CH2:11][CH2:10][CH:9]([CH:12]2[CH2:17][CH2:16][CH:15]([CH2:18][CH2:19][CH3:20])[CH2:14][CH2:13]2)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH:4]=[CH2:5].B1C2CCCC1CCC2.[OH:30]O.[OH-].[Na+]>C1COCC1>[CH2:18]([CH:15]1[CH2:16][CH2:17][CH:12]([CH:9]2[CH2:10][CH2:11][CH:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][OH:30])[CH2:7][CH2:8]2)[CH2:13][CH2:14]1)[CH2:19][CH3:20]

Participants

Conditions

Temperature: -20 °C

Procedure

4′-pent-4-enyl-4-propyl-bicyclohexyl [JP10046150] (9.9 g, 36 mmol) in THF (200 ml) are cooled to 0° C. and a 0.5 M solution of 9-BBN in THF (100 ml, 50 mmol) is added dropwise. The reaction is stirred overnight at room temp., cooled to −20° C. and 30% hydrogen peroxide (12 ml, 0.11 mol) are added followed by 32% aq. sodium hydroxide (7 ml, 76 mmol). The cooling bath is removed and the reaction is stirred overnight. Water is added and the mixture is extracted three times with ethyl acetate. The combined org. layers are washed with water and brine and are dried (Na2SO4). The solvent is evaporated and the crude product is recrystalised from ethanol to give 5-(4′-propyl-bicyclohexyl-4-yl)-pentan-1-ol as colourless crystals.

Workup

customThe cooling bath is removed
stirringthe reaction is stirred overnight
additionWater is added
extractionthe mixture is extracted three times with ethyl acetate
washlayers are washed with water and brine
dry with materialare dried (Na2SO4)
customThe solvent is evaporated
customthe crude product is recrystalised from ethanol

Sources & evidence

ORD record: ord-9cf25f8f0f1542dd8db4d3e9b430c4dd
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08372307B2

Reaction notes

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