Hydrochloric Acid → 2-Ethyl-2-((2-Hydroxymethylphenyl)thiomethyl)hexenal

HRID 478886Notes

Reaction equation

HRID 478886 reaction equation
[SH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5].[CH2:10]([C:12]([CH2:19]OS(C)(=O)=O)([CH2:15][CH2:16][CH2:17][CH3:18])[CH:13]=[O:14])[CH3:11].SC(O)C1C=CC=CC=1.Cl>C(N(CC)CC)C.COCCOCCOC>[CH2:10]([C:12]([CH2:19][S:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5])([CH:15]=[CH:16][CH2:17][CH3:18])[CH:13]=[O:14])[CH3:11]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1382782-MercaptobenzenemethanolHCID 5251295Mercaptobenzyl alcoholHCID 115722172-Ethyl-2-(mesyloxymethyl)hexanal

Product 1

HCID 544309312-Ethyl-2-((2-Hydroxymethylphenyl)thiomethyl)hexenalYield 107.8%

Reagents, catalysts & solvents 2

HCID 8150DiglymeSolventHCID 8471TriethylamineSolvent2×

Procedure

A mixture of 5.0 g (0.036 mole) of 2-mercaptobenzyl alcohol, 6.4 g (0.032 mole) of 1, 3.6 g (0.036 mole) of triethylamine and 25 mL of 2-methoxyethyl ether was held at reflux for 7 h. Additional 1.1 g of mercaptobenzyl alcohol and 0.72 g of triethylamine was added to the reaction mixture and the mixture was held at reflux for additional 16 h. The reaction mixture was cooled and poured into 6N HCl and extracted with methylene chloride. The methylene chloride extract was washed twice with 10% NaOH, dried over MgSO4 and concentrated in vacuo to give 9.6 g of residue. Purification by HPLC (20% EtOAc-hexane) gave 3.7 g (41%) of 16 as an oil.

Workup

  1. temperatureat reflux for 7 h
  2. temperatureat reflux for additional 16 h
  3. temperatureThe reaction mixture was cooled
  4. extractionextracted with methylene chloride
  5. extractionThe methylene chloride extract
  6. washwas washed twice with 10% NaOH
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f7dd7cd9bbc04888b4817b8ee5124c3b
Source dataset
uspto-grants-2003_11
Patent number
US06642268B2

Reaction notes

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