Formaldehyde → HCID 70606543, compound

HRID 46499Notes

Reaction equation

HRID 46499 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[CH2:7][C@@H:8]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][C@H:9]1[OH:18].[CH2:19]=O>C(O)=O.O.[OH-].[Na+].C(O)C>[CH3:19][N:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[CH2:7][C@@H:8]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][C@H:9]1[OH:18]

Participants

7

Reactant 2

HCID 712FormaldehydeHCID 70606663HCID 70606663, compound

Product 1

HCID 70606543HCID 70606543, compound

Reagents, catalysts & solvents 4

HCID 284Formic AcidSolventHCID 702EthanolSolventHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent2×

Procedure

trans-1,2,3,4-Tetrahydro-3-(2-piperidinylmethyl)-2-naphthalenol from Part D (21.5 g, 0.088 M) is dissolved in 20 ml 35% formaldehyde solution and 50 ml 98% formic acid. The mixture is heated overnight on a steam bath. The solution is taken to near dryness in vacuo. The residue is dissolved in water and basified with 50% NaOH solution. The material is extracted into chloroform, dried and the solvent is removed leaving a brown oil which shows a strong peak in the carbonyl region on the IR. This is dissolved in ethanol, NaOH solution is added and the mixture is heated for a few minutes on a steam bath. After diluting with ice water the mixture is extracted twice with ether. The ether extracts are dried and the solvent is removed leaving 23 g (quant) of the title compound.

Workup

  1. temperatureThe mixture is heated overnight on a steam bath
  2. extractionThe material is extracted into chloroform
  3. customdried
  4. customthe solvent is removed
  5. customleaving a brown oil which
  6. temperaturethe mixture is heated for a few minutes on a steam bath
  7. extractionis extracted twice with ether
  8. dry with materialThe ether extracts are dried
  9. customthe solvent is removed

Sources & evidence

ORD record
ord-e164381df13c48de90a37a2c2a14587a
Source dataset
uspto-grants-1979_11
Patent number
US04173640

Reaction notes

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