Dimethyl Sulfoxide → 16-Bromohexadec-5-ene

HRID 1380167

Reaction equation

[CH:1]([Br:17])=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].CS(C)=O.C([O-])(O)=O.[Na+]>>[CH2:1]([Br:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]=[CH:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

Reactant 3

HCID 679Dimethyl Sulfoxide

HCID 516892Sodium Bicarbonate

HCID 54030172Hexadecenyl bromide

Product 1

HCID 5444018716-Bromohexadec-5-ene

Conditions

Temperature: 60 °C

Procedure

Hexadecenyl bromide (360 g; 1.2 mol) and 1800 mL (2660 g; 34 mol) of DMSO were mixed and heated to 60° C. for 30 minutes. Then, NaHCO3 and a co-solvent were added, pressure reduced and temperature raised for the period of time specified in Table I. Reaction mixture was then cooled and concentrated on a rotary evaporator. GLC analysis was then carried out to determine aldehyde/alcohol ratios in the reaction product. Results from reactions employing several different co-solvents are summarized in Table I as runs 5-9.

Workup

temperaturetemperature raised for the period of time
customReaction mixture
temperaturewas then cooled
concentrationconcentrated on a rotary evaporator
customResults from reactions

Sources & evidence

ORD record: ord-96d7a0d1a2dc4bbdacb0e62356c65943
Source dataset: uspto-grants-1986_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04579977

Linked notes

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