Water → HCID 22152291, compound

HRID 1111334Notes

Reaction equation

HRID 1111334 reaction equation
C[O:2][C:3]1[C:13]([CH:14]=[O:15])=[CH:12][C:6]2[C:7]([CH3:11])([CH3:10])[CH2:8][O:9][C:5]=2[CH:4]=1.B(Br)(Br)Br.O>C(Cl)Cl>[OH:2][C:3]1[C:13]([CH:14]=[O:15])=[CH:12][C:6]2[C:7]([CH3:11])([CH3:10])[CH2:8][O:9][C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 22152283HCID 22152283, compound

Product 1

HCID 22152291HCID 22152291, compoundYield 59.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 10.4 g (50.4 mmol) of 2,3-dihydro-6-methoxy-3,3-dimethyl-5-benzofurancarboxaldehyde in 250 ml of methylene chloride and cooled to -78° C. was added dropwise 51.0 ml (51.0 mmol, 1M in methylene chloride) of boron tribromide. The reaction mixture was warmed to ambient temperature and stirred for 1 day. The reaction mixture was poured into 500 ml of water. The organic phase was washed with saturated sodium bicarbonate solution, dried and evaporated. The residue was chromatographed on silica gel (250 g) using a gradient from 2:1 (v/v) hexane:methylene chloride to methylene chloride as eluent. There was obtained 5.77 g (30.0 mmol, 59%) of 2,3-dihydro-6-hydroxy-3,3-dimethyl-5-benzofurancarboxaldehyde as a white solid mp 100°-102° C.

Workup

  1. washThe organic phase was washed with saturated sodium bicarbonate solution
  2. customdried
  3. customevaporated
  4. customThe residue was chromatographed on silica gel (250 g)

Sources & evidence

ORD record
ord-62969e298bd24a1f92cb738e16682ebe
Source dataset
uspto-grants-1990_12
Patent number
US04980352

Reaction notes

Loading…