Hydrochloric Acid → Ethyl 5-hydroxy-7-(2-methylphenyl)-1-oxo-1,3,4,7-tetrahydrobenzo[c]furan-6-carboxylate

HRID 979504Notes

Reaction equation

HRID 979504 reaction equation
C[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1C=O.C(N/[C:15](/[CH3:22])=[CH:16]\[C:17]([O:19][CH2:20][CH3:21])=[O:18])CCC.C([O:26][CH2:27][C:28](=O)[CH2:29][CH2:30][C:31]([O:33][CH2:34]C)=[O:32])(=O)C.Cl>O.C(O)C>[OH:26][C:27]1[CH2:28][C:29]2[CH2:34][O:33][C:31](=[O:32])[C:30]=2[CH:15]([C:22]2[CH:8]=[CH:9][CH:2]=[CH:3][C:6]=2[CH3:7])[C:16]=1[C:17]([O:19][CH2:20][CH3:21])=[O:18]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 107222-MethylbenzaldehydeHCID 10943541HCID 10943541, compoundHCID 11788689HCID 11788689, compound

Product 1

HCID 54699091Ethyl 5-hydroxy-7-(2-methylphenyl)-1-oxo-1,3,4,7-tetrahydrobenzo[c]furan-6-carboxylate

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

50 mmol of 2-methylbenzaldehyde, 50 mmol of ethyl 3-butylaminocrotonate and 50 mmol of ethyl 4-acetoxy-3-oxobutanecarboxylate together with 100 ml of ethanol were boiled under reflux overnight, then 10 ml of concentrated HCl and 20 ml of water were added, and the mixture was boiled for a further hour. The product is recrystallized from ethanol.

Workup

  1. temperatureunder reflux overnight
  2. waitthe mixture was boiled for a further hour
  3. customThe product is recrystallized from ethanol

Sources & evidence

ORD record
ord-208227d9998c4e80b6a8d7219a44ff64
Source dataset
uspto-grants-1987_05
Patent number
US04668691

Reaction notes

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