4-Hydroxybenzaldehyde → HCID 86139193, compound

HRID 901184Notes

Reaction equation

HRID 901184 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.Cl[S:11]([N:14]([CH3:16])[CH3:15])(=[O:13])=[O:12].CCOC(C)=O>CN(C1CCCCC1)C>[CH:6]([C:5]1[CH:8]=[CH:9][C:2]([O:1][S:11](=[O:13])(=[O:12])[N:14]([CH3:16])[CH3:15])=[CH:3][CH:4]=1)=[O:7]

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 8857Ethyl AcetateHCID 83372Dimethylsulphamoyl chloride

Product 1

HCID 86139193HCID 86139193, compound

Reagents, catalysts & solvents 1

HCID 7415N,N-DimethylcyclohexylamineSolvent

Conditions

Temperature
92.5 °C

Procedure

A stirred solution of 4-hydroxybenzaldehyde (1.0 g, 8.02 mmol) in N,N-dimethylcyclohexylamine (7 mL) was heated to 90-95° C. and at this temperature ClSO2NMe2 (0.87 mL, 8.02 mL) was added dropwise. The reaction mixture was then heated at 90-95° C. for 3 h. After cooling to room temperature, EtOAc (100 mL) was added and the organic layer was washed with 1M hydrochloric acid (2×100 mL) and then brine (3×50 mL), dried (Na2SO4), filtered and evaporated to give a yellow oil which solidified to a yellow wax upon storage in the refrigerator (1.82 g, 99%); 1H (270 MHz, CDCl3) 3.08 (6H, s), 7.46 (2H AA′BB′), 7.94 (2H AA′BB′) and 10.0 (1H, s).

Workup

  1. additionwas added dropwise
  2. temperatureAfter cooling to room temperature
  3. washthe organic layer was washed with 1M hydrochloric acid (2×100 mL)
  4. dry with materialbrine (3×50 mL), dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customto give a yellow oil which

Sources & evidence

ORD record
ord-a91b0f4b67ac49398b5910a6fdea7b37
Source dataset
uspto-grants-2008_04
Patent number
US07361677B2

Reaction notes

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