Carbon Dioxide → HCID 13070643, compound

HRID 1576255Notes

Reaction equation

HRID 1576255 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][CH:16]=1)[CH:6]([OH:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C([Li])CCC.[C:22](=O)=[O:23]>CCOCC.CCCCCC>[CH3:1][O:2][C:3]1[CH:16]=[CH:15][CH:14]=[C:5]2[C:4]=1[C:22](=[O:23])[O:13][CH:6]2[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 280Carbon Dioxide2×HCID 573301(3-Methoxyphenyl)(phenyl)methanolHCID 178418339Butyllithium

Product 1

HCID 13070643HCID 13070643, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8058HexaneSolvent

Procedure

To 3-methoxybenzhydrol (42.8 g.) in dry ether (800 ml.) is added 2.3 M. n-butyl lithium in hexane (250 ml.), dropwise with stirring under nitrogen. The deep red solution is stirred and heated under reflux for 2 hours and then poured into a stirred slurry of a large excess of solid carbon dioxide in ether and stirred until no carbon dioxide remains. The resulting suspension is extracted with water, the extract is acidified with concentrated hydrochloric acid, the precipitate is filtered off, washed with water, dried, and recrystallised from isopropanol to give 7-methoxy-3-phenylphthalide, m.p. 135°-138°C.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 2 hours
  3. extractionThe resulting suspension is extracted with water
  4. filtrationthe precipitate is filtered off
  5. washwashed with water
  6. customdried
  7. customrecrystallised from isopropanol

Sources & evidence

ORD record
ord-dd73aa6131d246759bd8e5fd057c0a21
Source dataset
uspto-grants-1976_09
Patent number
US03979513

Reaction notes

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