Hydrochloric Acid → 7-(Chloromethyl)-2,2-dimethyl-2,3-dihydro-1-benzofuran

HRID 1253230Notes

Reaction equation

HRID 1253230 reaction equation
[CH3:1][C:2]1([CH3:13])[CH2:6][C:5]2[CH:7]=[CH:8][CH:9]=[C:10]([CH2:11]O)[C:4]=2[O:3]1.[ClH:14]>O>[Cl:14][CH2:11][C:10]1[C:4]2[O:3][C:2]([CH3:13])([CH3:1])[CH2:6][C:5]=2[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 2795472(2,2-Dimethyl-2,3-dihydro-1-benzofuran-7-yl)methanol

Product 1

HCID 75374857-(Chloromethyl)-2,2-dimethyl-2,3-dihydro-1-benzofuran

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2,3-dihydro-2,2-dimethylbenzofuran-7-ylmethanol (6.3 grams, 0.035 mole) and concentrated hydrochloric acid (38%) was stirred at ambient temperature for 0.75 hour. The reaction mixture was diluted with water (50 ml) and extracted with diethyl ether. The extract was washed successively with a 10% aqueous solution of sodium hydroxide and a saturated aqueous sodium chloride solution. The dried (sodium sulfate) extract was concentrated under reduced pressure, yielding 7-chloromethyl-2,3-dihydro-2,2-dimethylbenzofuran. The NMR spectrum was consistent with the proposed structure.

Workup

  1. extractionextracted with diethyl ether
  2. washThe extract was washed successively with a 10% aqueous solution of sodium hydroxide
  3. dry with materialThe dried (sodium sulfate)
  4. extractionextract
  5. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-29ae23e0555a4006b0932f71d9088e12
Source dataset
uspto-grants-1988_05
Patent number
US04748186

Reaction notes

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