Ethylene Glycol → 5-Benzyloxy-2,2-dimethyl-7-(1,1-dimethylheptyl)-3,4-dihydro-2H-benzopyran-4-carboxylic acid

HRID 1153913Notes

Reaction equation

HRID 1153913 reaction equation
[CH2:1]([O:8][C:9]1[C:14]2C(C#N)[CH2:16][C:17]([CH3:20])([CH3:19])[O:18][C:13]=2[CH:12]=[C:11]([C:23]([CH3:31])([CH3:30])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-:32].[K+].[CH2:34]([OH:37])[CH2:35]O.Cl>C(OCC)C>[CH2:1]([O:8][C:9]1[C:14]2[CH:35]([C:34]([OH:37])=[O:32])[CH2:16][C:17]([CH3:20])([CH3:19])[O:18][C:13]=2[CH:12]=[C:11]([C:23]([CH3:31])([CH3:30])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 133645735-benzyloxy-4-cyano-2,2-dimethyl-7-(1,1-dimethylheptyl)-3,4-dihydro-2H-benzopyran

Product 1

HCID 133645785-Benzyloxy-2,2-dimethyl-7-(1,1-dimethylheptyl)-3,4-dihydro-2H-benzopyran-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2.0 g 5-benzyloxy-4-cyano-2,2-dimethyl-7-(1,1-dimethylheptyl)-3,4-dihydro-2H-benzopyran, 20 g potassium hydroxide and 100 ml ethylene glycol are heated under nitrogen at reflux for 18 hours and cooled to ambient temperature. The mixture is acidified to pH 3 with concentrated hydrochloric acid, extracted with ethyl acetate and the extracts dried (MgSO4). Evaporation of solvent gives an oil which is taken up in ethyl ether, washed with water, brine, dried (MgSO4) and the solvent evaporated to give 2.09 g of crude solid. The crude was purified by chromatography on silica gel, eluting with ethyl ether/hexane. The combined product fractions are combined and solvent evaporated to afford 1.69 g of the product, m.p. 137°-138° C.

Workup

  1. temperatureare heated under nitrogen
  2. temperatureat reflux for 18 hours
  3. extractionextracted with ethyl acetate
  4. dry with materialthe extracts dried (MgSO4)
  5. customEvaporation of solvent
  6. customgives an oil which
  7. washwashed with water, brine
  8. dry with materialdried (MgSO4)
  9. customthe solvent evaporated
  10. customto give 2.09 g of crude solid
  11. customThe crude was purified by chromatography on silica gel
  12. washeluting with ethyl ether/hexane
  13. customsolvent evaporated

Sources & evidence

ORD record
ord-2461269067a84cd7abfa4996eae01b23
Source dataset
uspto-grants-1984_12
Patent number
US04486428

Reaction notes

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