Ethanol → HCID 58935107, compound

HRID 970254Notes

Reaction equation

HRID 970254 reaction equation
[Br-].[CH2:2]([O:8][C:9]1[CH:34]=[CH:33][C:12]([CH2:13][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:11][CH:10]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].O.[CH2:36]([OH:38])[CH3:37]>>[OH:38][CH2:36][C:37]1[CH:34]=[CH:33][C:12](/[CH:13]=[CH:13]/[C:12]2[CH:11]=[CH:10][C:9]([O:8][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])=[CH:34][CH:33]=2)=[CH:11][CH:10]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 962WaterHCID 85675261HCID 85675261, compound

Product 1

HCID 58935107HCID 58935107, compoundYield 37%

Procedure

115 mg (16.5 mmole) of Li were dissolved in 75 ml of ethanol under a nitrogen atmosphere. Then 2.05 g (15 mmole) of aldehyde 4-hydroxymethylbenzaldehyde were added and the mixture was cooled in an ice bath. Then 5.148 g (15 mmole) of (4-hexyloxy-benzyl)-triphenylphosphonium bromide were added. The mixture was stirred in the ice bath under nitrogen for 0.5 hour, and then stirred at room temperature for 3 hours. 2.5 ml of water were added and the precipitate was collected on a filter and washed with 10 ml of ethanol. After drying over silica in a dessicator, 1.75 g of a white powder were obtained. Yield 37%.

Workup

  1. temperaturethe mixture was cooled in an ice bath
  2. customthe precipitate was collected on
  3. filtrationa filter
  4. washwashed with 10 ml of ethanol
  5. customAfter drying over silica in a dessicator

Sources & evidence

ORD record
ord-65e2a4a83f61428b8761f0293feb7ce8
Source dataset
uspto-grants-2007_12
Patent number
US07311948B2

Reaction notes

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