Ethylene Glycol → HCID 774818, compound

HRID 1428147Notes

Reaction equation

HRID 1428147 reaction equation
[CH:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1)=O.[CH2:13]([OH:16])[CH2:14][OH:15].C(OCC)(OCC)OCC>C([O-])(O)=O.[Na+]>[O:15]1[CH2:14][CH2:13][O:16][CH:1]1[C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 15294Methyl 4-FormylbenzoateHCID 31214Ethyl orthoformate

Product 1

HCID 774818HCID 774818, compound

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

Methyl 4-formylbenzoate (3.28 g, 20.0 mmol) was suspended in ethylene glycol (4.46 mL, 80.0 mmol), then successively treated with triethyl orthoformate (3.66 mL, 22.0 mmol) and Me3NPhBr3 (376 mg, 1.00 mmol) at 22° C.; within 5 min, all solids dissolved. The resulting orange solution was stirred 0.5 h, then diluted with saturated aqueous NaHCO3 (50 mL), transferred to separatory funnel and washed with EtOAc (3×50 mL). The combined EtOAc washes were dried over MgSO4, filtered and concentrated in vacuo to a colorless oil (Rf 0.4 in 4:1 pentane/EtOAc, KMnO4). This material was used without further purification in the subsequent reduction step.

Workup

  1. dissolutionall solids dissolved
  2. customtransferred to separatory funnel
  3. washwashed with EtOAc (3×50 mL)
  4. dry with materialThe combined EtOAc washes were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo to a colorless oil (Rf 0.4 in 4:1 pentane/EtOAc, KMnO4)
  7. customThis material was used without further purification in the subsequent reduction step

Sources & evidence

ORD record
ord-0e85cc66cde443b98aa3123e6198bb06
Source dataset
uspto-grants-2015_01
Patent number
US08936777B2

Reaction notes

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