Hydrochloric Acid → Ethyl 4-phenoxybenzoylformate

HRID 1384467Notes

Reaction equation

HRID 1384467 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[O:5]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.Cl[C:19](=[O:25])[C:20]([O:22][CH2:23][CH3:24])=[O:21].Cl>C(Cl)Cl>[CH2:23]([O:22][C:20](=[O:21])[C:19]([C:9]1[CH:10]=[CH:11][C:6]([O:5][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[CH:7][CH:8]=1)=[O:25])[CH3:24]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7583Diphenyl EtherHCID 20884Ethoxalyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 2758881Ethyl 4-phenoxybenzoylformateYield 83.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 301 g (2.26 mol) of AlCl3 in CH2Cl2 (750 ml) a mixture of 383 g (2.25 mol) of 4-phenoxybenzene and 205 g (1.50 mol) of ethyl chloroglyoxylate in CH2Cl2 (750 ml) is added dropwise at ice-bath temperature during one hour. Thereafter, the mixture is gradually warmed up to room temperature and stirred overnight. Then, the reaction mixture is poured onto ice. The aq. solution is acidified to pH 3 with aqueous HCl solution, followed by an extraction with CH2Cl2. The extract is dried over anhydrous MgSO4. The desired product is purified by silica gel column chromatography using CH2Cl2-hexane mixture as eluent. 338 g of colorless oily 4-phenoxyphenyl glyoxylic acid ethyl ester is obtained (83%).

Workup

  1. additionis added dropwise at ice-bath temperature during one hour
  2. additionThen, the reaction mixture is poured onto ice
  3. extractionfollowed by an extraction with CH2Cl2
  4. dry with materialThe extract is dried over anhydrous MgSO4
  5. customThe desired product is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-bb4f6533e47841e1b8f7bf405043857e
Source dataset
uspto-grants-2001_07
Patent number
US06258954B1

Reaction notes

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