Formaldehyde → Ethyl 4-(4-hydroxy-3-oxobutyl)benzoate

HRID 1656564Notes

Reaction equation

HRID 1656564 reaction equation
[C:1]([C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][CH:14]=[O:15])=[CH:8][CH:7]=1)([O:3][CH2:4][CH3:5])=[O:2].[CH2:16]=[O:17].[Br-].C(C1SC2C=CC=CC=2[NH+]=1)C.C(N(CC)CC)C>C(O)C>[OH:17][CH2:16][C:14](=[O:15])[CH2:13][CH2:12][C:9]1[CH:10]=[CH:11][C:6]([C:1]([O:3][CH2:4][CH3:5])=[O:2])=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 8471TriethylamineHCID 2757377Ethyl 4-(3-oxopropyl)benzoateHCID 68772949Ethyl benzothiazolium bromide

Product 1

HCID 10609833Ethyl 4-(4-hydroxy-3-oxobutyl)benzoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1.1 g (5 mmol) of 3-(4-carbethoxyphenyl)propanal and 150 mg (5 mmol) of paraformaldehyde in 10 mL of ethanol, together with 230 mg (0.9 mmol) of ethyl benzothiazolium bromide and 90 mg (0.9 mmol) of triethylamine, is heated at about 70° C. for 16 hours. The reaction mixture is concentrated in vacuo and the product further purified by chromatography on silica gel, eluting with 15:85 ethyl acetate:hexane, to yield ethyl 4-(4-hydroxy-3-oxobutyl)benzoate as a colorless oil which solidifies upon standing; m.p. 51°-52° C. Anal. calcd for C13H16O4 : C, 66.09; H 6.83. Found: C, 66.29; H, 6.70.

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. customthe product further purified by chromatography on silica gel
  3. washeluting with 15:85 ethyl acetate

Sources & evidence

ORD record
ord-b84a1bc7fcda459b8fc671faf878f9be
Source dataset
uspto-grants-1993_10
Patent number
US05254687

Reaction notes

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