Hydrochloric Acid → Ethyl 4-(phenylmethoxy)benzoate

HRID 866387Notes

Reaction equation

HRID 866387 reaction equation
N[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.Cl.N([O-])=O.[Na+].[C:18]([C:21]1[CH:34]=[CH:33][C:24](OCC2C=CC=CC=2)=[CH:23][CH:22]=1)(O)=[O:19]>CCOCC.O>[CH2:9]([O:8][C:6]([C:5]1[CH:11]=[CH:12][C:2]([O:19][CH2:18][C:21]2[CH:34]=[CH:33][CH:24]=[CH:23][CH:22]=2)=[CH:3][CH:4]=1)=[O:7])[CH3:10]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 2337BenzocaineHCID 738804-(Benzyloxy)benzoic acidHCID 23668193Sodium Nitrite

Product 1

HCID 191414Ethyl 4-(phenylmethoxy)benzoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

Ethyl 4-aminobenzoate (8.25g) in a mixture of conc. hydrochloric acid (12.5ml) and water (12.5ml.) at 0° C was diazotised by the addition of sodium nitrite (3.45g). The solution of the diazo compound was added to benzyl alcohol (20g) at 35° C with stirring then stirred at this temperature for 3hr. The reaction mixture was cooled and 4-ethoxycarbonylphenoxy phenyl methane isolated by extraction with ether, m.p. 45° C.

Workup

  1. stirringthen stirred at this temperature for 3hr
  2. temperatureThe reaction mixture was cooled

Sources & evidence

ORD record
ord-034c6a13e6d24e6a899da802273e45ad
Source dataset
uspto-grants-1978_07
Patent number
US04098816

Reaction notes

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