Water → HCID 20553066, compound

HRID 1446853Notes

Reaction equation

HRID 1446853 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=[O:6].[OH2:11].[C:12]([O:18][CH2:19]Cl)(=[O:17])[C:13]([CH3:16])([CH3:15])[CH3:14]>CN(C=O)C.C(N(CC)CC)C>[C:12]([O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH2:19][O:18][C:12](=[O:17])[C:13]([CH3:16])([CH3:15])[CH3:14])[CH:5]=[O:6])(=[O:11])[C:13]([CH3:16])([CH3:15])[CH3:14]

Participants

6

Reactant 3

HCID 962WaterHCID 87683,4-DihydroxybenzaldehydeHCID 87885Chloromethyl pivalate2×

Product 1

HCID 20553066HCID 20553066, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent2×

Procedure

3,4-Dihydroxybenzaldehyde (27.6 g, 0.2 mol) was dissolved in 100 mL of DMF with 45 mL of triethylamine and 40 mL of pivalyloxymethyl chloride. The mixture was stirred at room temperature for five days. After one day 20 mL of pivalyloxymethyl chloride and 20 ml of triethylamine were added to the mixture. The mixture was then poured into 600 mL of water. The water was extracted with 600 mL of CH2Cl2 and twice with 500 mL of ether. The organic layers were concentrated and that residue was chromatographed on silicAr CC-7 using petroleum ether bp 30°-60°, acetone (1:1) as the eluent to give the desired compound: mp 58°-60°.

Workup

  1. extractionThe water was extracted with 600 mL of CH2Cl2 and twice with 500 mL of ether
  2. concentrationThe organic layers were concentrated and that residue
  3. customwas chromatographed on silicAr CC-7

Sources & evidence

ORD record
ord-ae17dd38811e424ea1a9463fe4ebb171
Source dataset
uspto-grants-1982_02
Patent number
US04313956

Reaction notes

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