4-Hydroxybenzaldehyde → 4-(((4-Methylphenyl)sulfonyl)oxy)benzaldehyde

HRID 1827511Notes

Reaction equation

HRID 1827511 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.C(N(CC)CC)C.[S:17](Cl)([C:20]1[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=1)(=[O:19])=[O:18].Cl>ClCCl.O>[CH:6]([C:5]1[CH:8]=[CH:9][C:2]([O:1][S:17]([C:20]2[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=2)(=[O:19])=[O:18])=[CH:3][CH:4]=1)=[O:7]

Participants

7

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 8471Triethylamine

Product 1

HCID 51250864-(((4-Methylphenyl)sulfonyl)oxy)benzaldehydeYield 71%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-hydroxybenzaldehyde (5.93 g, 48.56 mmol) and triethylamine (10 mL) in 50 mL of dichloromethane was added tosyl chloride (11.8 g, 61.89 mmol). The reaction mixture was stirred at room temperature for 24 hr. The reaction mixture was diluted with water, acidified with 1 N HCl, and extracted into methylene chloride. The organic layer was separated, dried over magnesium sulfate, and concentrated. The residue was purified by silica gel chromatography (9:1 hexanes:ethyl acetate to 5:1 hexanes:ethyl acetate) to afford 9.50 g (71%) of the title compound of Step A. 1HNMR (CDCl3): δ 9.81 (s, 1H), 7.69 (d, 2H, J=8.8 Hz), 7.57 (d, 2H, J=8.4 Hz), 7.19 (d, 2H, J=8.4 Hz), 7.03 (d, 2H, J=8.4 Hz), and 2.28 (s, 3H).

Workup

  1. extractionextracted into methylene chloride
  2. customThe organic layer was separated
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography (9:1 hexanes:ethyl acetate to 5:1 hexanes:ethyl acetate)

Sources & evidence

ORD record
ord-5dacf3441c4d416fb628f985983659fe
Source dataset
uspto-grants-2006_05
Patent number
US07053212B2

Reaction notes

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