Tetrahydrofuran → (3-Acetyloxy-5-carbonochloridoylphenyl) acetate

HRID 1373170Notes

Reaction equation

HRID 1373170 reaction equation
[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([O:14][C:15](=[O:17])[CH3:16])[CH:13]=1)[C:8](O)=[O:9])(=[O:3])[CH3:2].C1COCC1.C(Cl)(=O)C([Cl:26])=O>ClCCl>[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([O:14][C:15](=[O:17])[CH3:16])[CH:13]=1)[C:8]([Cl:26])=[O:9])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 65578Oxalyl chlorideHCID 5398693,5-Diacetoxybenzoic Acid

Product 1

HCID 11368883(3-Acetyloxy-5-carbonochloridoylphenyl) acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3,5-Diacetoxybenzoic acid (15 g, 63 mM) was suspended in dichloromethane (100 mls), THF(20 mls) with oxalyl chloride (7.34 mls, 69.3 mM) and DMF(2–3 drops) added. The resultant mixture was stirred for three hours at ambient temperature in a flask fitted with a gas bubbler. This gave a pale brown solution. After concentration ‘in vacuo’ the residue was triturated with diethyl ether. This gave a colourless solid, 3,5-diacetoxybenzoyl chloride (15.95 g) which was used for the next stage without further purification.

Workup

  1. customfitted with a gas bubbler
  2. customThis gave a pale brown solution
  3. concentrationAfter concentration ‘in vacuo’ the residue
  4. customwas triturated with diethyl ether

Sources & evidence

ORD record
ord-88aa912c3f694f51bcde1212e495c1e7
Source dataset
uspto-grants-2007_01
Patent number
US07160906B2

Reaction notes

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