2,4-Dihydroxybenzaldehyde → HCID 21841045, compound

HRID 1739467Notes

Reaction equation

HRID 1739467 reaction equation
C(N(CC)CC)C.[OH:8][C:9]1[CH:16]=[C:15]([OH:17])[CH:14]=[CH:13][C:10]=1[CH:11]=[O:12].[C:18]([C:22](Cl)=[O:23])([CH3:21])([CH3:20])[CH3:19].C(OCC)(=O)C>ClCCl.CCCCCC>[C:18]([C:22]([O:17][C:15]1[CH:14]=[CH:13][C:10]([CH:11]=[O:12])=[C:9]([OH:8])[CH:16]=1)=[O:23])([CH3:21])([CH3:20])[CH3:19]

Participants

7

Reactant 4

HCID 72132,4-DihydroxybenzaldehydeHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 62493Pivaloyl chloride

Product 1

HCID 21841045HCID 21841045, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

Triethylamine (5 ml) was added to a stirred suspension of 2,4-dihydroxybenzaldehyde (12 g) in dichloromethane (50 ml) at -8° C. To this mixture was added t-butylcarbonyl chloride (4.4 ml) and the mixture was allowed to warm to ambient temperature and was stirred at this temperature for 16 hours. The reaction mixture was washed consecutively with aqueous 1N hydrochloric acid (20 ml), water (20 ml) and saturated aqueous sodium bicarbonate solution (20 ml) and then dried (MgSO4). The residue obtained on removal of the solvent was subjected to chromatography on silica eluting with a mixture of ethyl acetate and hexane (1:9 v/v) to give 4-(t-butylcarbonyloxy)-2-hydroxy-benzaldehyde (5.82 g; 35%).

Workup

  1. washThe reaction mixture was washed consecutively with aqueous 1N hydrochloric acid (20 ml), water (20 ml) and saturated aqueous sodium bicarbonate solution (20 ml)
  2. dry with materialdried (MgSO4)
  3. customThe residue obtained on removal of the solvent

Sources & evidence

ORD record
ord-812ea42dbc1b4232a5211902738524b0
Source dataset
uspto-grants-1999_10
Patent number
US05965741

Reaction notes

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