1-Propanol → HCID 23282392, compound

HRID 369665Notes

Reaction equation

HRID 369665 reaction equation
[CH2:1]([C:3]1[CH:17]=[C:16]([O:18][CH2:19][CH:20]=[C:21]([Cl:23])[Cl:22])[CH:15]=[C:14]([CH2:24][CH3:25])[C:4]=1[O:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][CH2:11][CH:12]=[O:13])[CH3:2].[CH2:26]([OH:29])[CH2:27][CH3:28].[CH2:30]1[CH2:35]CCC[CH2:31]1>>[CH2:24]([C:14]1[CH:15]=[C:16]([O:18][CH2:19][CH:20]=[C:21]([Cl:22])[Cl:23])[CH:17]=[C:3]([CH2:1][CH3:2])[C:4]=1[O:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][CH2:11][CH:12]([O:29][CH2:26][CH2:27][CH3:28])[O:13][CH2:31][CH2:30][CH3:35])[CH3:25]

Participants

4

Reactant 3

HCID 10311-PropanolHCID 8078CyclohexaneHCID 54234953HCID 54234953, compound

Product 1

HCID 23282392HCID 23282392, compoundYield 77%

Procedure

A mixture of 0.39 g of 4-(2,6-diethyl-4-(3,3-dichloro-2-propenyloxy)phenoxy)butyloxyacetaldehyde, 0.24 g of 1-propanol and 10 ml of cyclohexane was stirred at room temperature, to which 0.038 g of p-tolunesulfonic acid hydrate and 0.40 g of powdered molecular sieves SA were added. After stirring at room temperature for 30 minutes, the reaction mixture was filtered. The filtrate was added to water and extracted twice with diethyl ether. The diethyl ether layers were combined, washed with water, dried over magnesium sulfate and then evaporated to give a crude product. The crude product was subjected to silica gel chromatography, which afforded 0.38 g of 3,5-diethyl-1-(3,3-dichloro-2-propenyloxy)-4-(4-(2,2-dipropyloxyethoxy)butyloxy)benzene (yield, 77%), nD23.5 1.4975.

Workup

  1. additionwere added
  2. filtrationthe reaction mixture was filtered
  3. additionThe filtrate was added to water
  4. extractionextracted twice with diethyl ether
  5. washwashed with water
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. customto give a crude product

Sources & evidence

ORD record
ord-c002f199ad7048019995fd2b7cf11600
Source dataset
uspto-grants-2000_10
Patent number
US06140274

Reaction notes

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