3-Hydroxybenzaldehyde → 3-formylphenyl 2-acetoxybenzoate

HRID 1636079Notes

Reaction equation

HRID 1636079 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].C(N([CH2:15][CH3:16])CC)C.[C:17](Cl)(=[O:25])[C:18]1[C:19](=[CH:21][CH:22]=[CH:23][CH:24]=1)[OH:20].[OH2:27]>C(Cl)Cl>[CH:5]([C:4]1[CH:3]=[C:2]([O:1][C:17](=[O:25])[C:18]2[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=2[O:20][C:15](=[O:27])[CH3:16])[CH:9]=[CH:8][CH:7]=1)=[O:6]

Participants

6

Reactant 4

HCID 1013-HydroxybenzaldehydeHCID 962WaterHCID 8471TriethylamineHCID 74041Salicyloyl chloride

Product 1

HCID 107793803-formylphenyl 2-acetoxybenzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-hydroxybenzaldehyde (830 g) and triethylamine (8.24 g) in methylene chloride (12.6 l) is kept under stirring, in inert nitrogen atmosphere, cooling at a temperature between −5° C. and 0° C. Salicyloyl chloride (1650 g) is added in small portions in an hour. The mixture is still kept under stirring for 15 minutes, then water (10 l) is added and the phases are separated. The aqueous phase is recovered and apart extracted with methylene chloride (3 l). The organic phases are joined together, washed with a 5% Na2CO3 solution (5 l×2 times) and then with water (5 l×2 times). The organic phase is dried with magnesium sulphate (2 Kg) in the presence of decolorating carbon (300 g). It is filtered under vacuum and the solvent is evaporated at reduced pressure at a bath temperature lower than 40° C., at last obtaining 1929 g of 3-(formyl)phenyl ester of the 2-(acetoxy) benzoic acid (quantitative yield) m.p. 80-84° C. The compound purity determined by HPLC, by using a LiChrospher® 100 RP 8 column, eluent buffer phosphate pH 8/acetonitrile 55/45, was equal to 98.5%.

Workup

  1. temperaturecooling at a temperature between −5° C. and 0° C
  2. stirringunder stirring for 15 minutes
  3. customthe phases are separated
  4. customThe aqueous phase is recovered
  5. extractionapart extracted with methylene chloride (3 l)
  6. washwashed with a 5% Na2CO3 solution (5 l×2 times)
  7. dry with materialThe organic phase is dried with magnesium sulphate (2 Kg) in the presence of decolorating carbon (300 g)
  8. filtrationIt is filtered under vacuum
  9. customthe solvent is evaporated at reduced pressure at a bath temperature lower than 40° C.

Sources & evidence

ORD record
ord-1028189451b14532baa4b5a220a4fb32
Source dataset
uspto-grants-2003_01
Patent number
US06512137B1

Reaction notes

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