O-Xylene → HCID 53946766, compound

HRID 1737158Notes

Reaction equation

HRID 1737158 reaction equation
[C:1]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Br[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([OH:30])=[O:29].[C:31]1(C)[C:32]([CH3:37])=[CH:33][CH:34]=CC=1>>[CH3:1][C:32]([CH3:37])([CH3:31])[CH2:33][CH:34]=[CH:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([OH:30])=[O:29]

Participants

4

Reactant 3

HCID 7237O-XyleneHCID 11776TriphenylphosphineHCID 5482758-Bromooctanoic acid

Product 1

HCID 53946766HCID 53946766, compound

Procedure

8-triphenylphosphonium octanoic acid bromide salt (2.43 g) was prepared by reacting triphenyl phosphine with 8-bromooctanoic acid in xylene solvent under reflux conditions, and removing the solvent. The residue was dissolved in THF (20 ml)/DMSO (2 ml) and butyllithium (2.5M; 4 ml) in hexane (4 ml) was added dropwise at 0° C. After warming to room temperature over 30 minutes 3,3-dimethylbutanal (0.5 g) in THF (5 ml) was added dropwise and the mixture stirred at room temperature for 3 hours. Water and dilute hydrochloric acid were added and the mixture extracted with diethyl ether(x3). Pure product 11,11-dimethyldodecan-8-enoic acid (0.4 g) was provided after silica gel column chromatography.

Workup

  1. customremoving the solvent
  2. dissolutionThe residue was dissolved in THF (20 ml)/DMSO (2 ml) and butyllithium (2.5M; 4 ml) in hexane (4 ml)
  3. additionwas added dropwise at 0° C
  4. additionwas added dropwise
  5. additionWater and dilute hydrochloric acid were added
  6. extractionthe mixture extracted with diethyl ether(x3)

Sources & evidence

ORD record
ord-4c47943e7bbc4bc3ad4898444c93ad71
Source dataset
uspto-grants-1999_10
Patent number
US05962002

Reaction notes

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