HCID 21276841, compound → HCID 20086457, compound
Reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8]O)[C:5]([CH2:10][CH2:11][OH:12])=[CH:4][CH:3]=1>P(=O)(O)(O)O.O>[Cl:1][C:2]1[CH:7]=[C:6]2[C:5]([CH2:10][CH2:11][O:12][CH2:8]2)=[CH:4][CH:3]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
2-(4-Chloro-6-hydroxymethylphenyl)ethanol (45 g) was dissolved in orthophosphoric acid (200 ml) and the solution was heated at 100° for 2 hr. The cooled reaction mixture was diluted with water (1 liter), extracted with ether (4×200 ml) and the combined ether extract was washed with sodium hydrogen carbonate solution (10% w/v 2×200 ml) and water (200 ml) and then dried (magnesium sulphate) and decolourised with activated carbon and evaporated in vacuo to afford 7-chloroisochroman as an oil, (30 g), characterised by its nmr spectrum.
Workup
- temperaturethe solution was heated at 100° for 2 hr
- customThe cooled reaction mixture
- extractionextracted with ether (4×200 ml)
- extractionthe combined ether extract
- washwas washed with sodium hydrogen carbonate solution (10% w/v 2×200 ml) and water (200 ml)
- dry with materialdried (magnesium sulphate)
- customevaporated in vacuo
Sources & evidence
- ORD record
- ord-1b33f4bb1729448d8167fd0b2f6a7c7d
- Source dataset
- uspto-grants-1989_01
- Patent number
- US04801593
Reaction notes
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