Triethylamine → HCID 21841052, compound

HRID 2395007Notes

Reaction equation

HRID 2395007 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:3]=1[CH:4]=[O:5].C(N(CC)CC)C.[C:18](Cl)(=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20]>ClCCl>[OH:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][C:18]([C:19]([CH3:22])([CH3:21])[CH3:20])=[O:23])=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 709492,5-Dihydroxybenzaldehyde

Product 1

HCID 21841052HCID 21841052, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2,5-dihydroxybenzaldehyde (10 g) in dichloromethane (50 ml) at 0° C. was added triethylamine (5 ml) and pivaloyl chloride (4.4 ml). The mixture was stirred at room temperature for 18 hours, filtered and the filtrates washed with 2M HCl (100 ml), brine (100 ml) and sodium bicarbonate (100 m), dried (magnesium sulphate) filtered and evaporated. The residue was purified by chromatography on silica gel using dichloromethane:hexane (0:1 to 1:1 gradient) then ethyl acetate:hexane (1:9 to 3:7 gradient) as eluants to give 2-hydroxy-5-(t-butylcarbonyloxy)benzaldehyde (4 g) and some 2,5-dihydroxy-benzaldehyde.

Workup

  1. filtrationfiltered
  2. washthe filtrates washed with 2M HCl (100 ml), brine (100 ml) and sodium bicarbonate (100 m)
  3. dry with materialdried (magnesium sulphate)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-48b3adca75d5428f8326a24f6b634664
Source dataset
uspto-grants-1998_09
Patent number
US05811459

Reaction notes

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