Sulfuric Acid → HCID 19063061, compound

HRID 1957703Notes

Reaction equation

HRID 1957703 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].ClCCl.[C:14]12(O)[CH2:23][CH:18]3[CH2:19][CH:20]([CH2:22][CH:16]([CH2:17]3)[CH2:15]1)[CH2:21]2.S(=O)(=O)(O)O>O>[C:14]12([C:7]3[C:8]([OH:10])=[CH:9][C:2]([OH:1])=[C:3]([CH:6]=3)[CH:4]=[O:5])[CH2:23][CH:18]3[CH2:19][CH:20]([CH2:22][CH:16]([CH2:17]3)[CH2:15]1)[CH2:21]2

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 6344DichloromethaneHCID 72132,4-DihydroxybenzaldehydeHCID 641521-Adamantanol

Product 1

HCID 19063061HCID 19063061, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

40 g (0.29 mol) of 2,4-dihydroxybenzaldehyde, 600 ml of dichloromethane and 46.4 g (0.34 mol) of 1-adamantanol were introduced into a round-bottomed flask and 24 ml of concentrated sulfuric acid were added. The reaction medium was stirred at room temperature for twelve hours and was then poured into water. The organic phase was separated out after settling had taken place, dried over magnesium sulfate and evaporated. The residue obtained was purified by chromatography on a column of silica, eluted with dichloromethane. 50.8 g (64%) of the expected aldehyde, having a melting point of 259°-61° C., were recovered.

Workup

  1. customThe organic phase was separated out
  2. dry with materialdried over magnesium sulfate
  3. customevaporated
  4. customThe residue obtained
  5. customwas purified by chromatography on a column of silica
  6. washeluted with dichloromethane
  7. customwere recovered

Sources & evidence

ORD record
ord-ec1cde92e2c345fd9c4e1950eb8b6743
Source dataset
uspto-grants-1998_07
Patent number
US05786379

Reaction notes

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