Hydrochloric Acid → 5-Bromo-2,3-dihydro-3,3-dimethyl-2-hydroxybenzofuran

HRID 1155952Notes

Reaction equation

HRID 1155952 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([Br:9])=[CH:5][C:4]=1[C:10]([CH3:14])([CH3:13])[CH2:11][OH:12].Cl.N1C=CC=CC=1.Cl>CCOCC>[Br:9][C:6]1[CH:7]=[CH:8][C:3]2[O:2][CH:11]([OH:12])[C:10]([CH3:14])([CH3:13])[C:4]=2[CH:5]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10176127Pyridinium chlorideHCID 234641502-(5-Bromo-2-methoxyphenyl)-2-methylpropan-1-ol

Product 1

HCID 205362245-Bromo-2,3-dihydro-3,3-dimethyl-2-hydroxybenzofuran

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

2-(2-(Methoxy-5-bromophenyl)-2-methyl-1-propanol (30 g, 0.115 mole) was added to molten pyridine hydrochloride (60 g) and the mixture heated with stirring at 190°-200° C. for 50 minutes. Addition to ice-water containing a little hydrochloric acid and isolated through ether gave, after recrystallisation from petroleum ether (b.p. 80°-100° C.) 11.7 g (42%) title product m.p. 114°-5° C.

Workup

  1. temperaturethe mixture heated
  2. customgave
  3. customafter recrystallisation from petroleum ether (b.p. 80°-100° C.) 11.7 g (42%) title product m.p. 114°-5° C.

Sources & evidence

ORD record
ord-cfeba724d88d4fe19c6b5624b66fb900
Source dataset
uspto-grants-1982_06
Patent number
US04333759

Reaction notes

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