Ammonium Chloride → HCID 18521522, compound

HRID 413678Notes

Reaction equation

HRID 413678 reaction equation
[CH3:1][O:2][CH2:3][Mg]Cl.[C:6]([CH:9]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[CH2:13][CH2:12][C:11]2[CH:20]=[CH:21][CH:22]=[CH:23][C:10]1=2)(=O)[CH3:7].[Cl-].[NH4+]>O1CCCC1>[CH3:1][O:2][CH2:3][C:6](=[C:9]1[C:10]2[CH:23]=[CH:22][CH:21]=[CH:20][C:11]=2[CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]1=2)[CH3:7]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 14896946HCID 14896946, compoundHCID 178496729HCID 178496729, compound

Product 1

HCID 18521522HCID 18521522, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of methoxymethyl magnesiumchloride in dry tetrahydrofuran (prepared from methoxymethyl chloride (16.1 g, 0.2 mol), magnesium turnings (4.8 g, 0.2 mol), mercury chloride (0.25 g) and dry tetrahydrofuran (30 ml)) was cooled on an ice-salt bath to −10° C. A solution of 5-acetyl-10,11-dihydro-5H-dibenzo[a,d]cycloheptene (21.4 g, 0.09 mol, prepared as described in Belg., 609, 095, 1962) in dry tetrahydrofuran (50 ml) was added drop-wise. When addition was complete the mixture was stirred for 1 h. Saturated ammonium chloride (150 ml) was carefully added and the mixture was extracted with diethyl ether (2×100 ml). The combined extracts were dried (MgSO4) and the solvent was evaporated in vacuo to give a residue which was fractionally distilled. The fraction collected at b.p. 130-140° C./70 Pa was purified by gradient column chromatography on silica gel (80 g) using cyclohexane and then benzene as eluents. The benzene fraction afforded 9.4 g of crude 5-(1-methoxymethylethylidene)-10,11-dihydro-5H-dibenzo[a,d]cycloheptene as an oil.

Workup

  1. additionWhen addition
  2. extractionthe mixture was extracted with diethyl ether (2×100 ml)
  3. dry with materialThe combined extracts were dried (MgSO4)
  4. customthe solvent was evaporated in vacuo
  5. customto give a residue which
  6. distillationwas fractionally distilled
  7. customThe fraction collected at b.p. 130-140° C./70 Pa
  8. customwas purified by gradient column chromatography on silica gel (80 g)

Sources & evidence

ORD record
ord-c8d836e6c6ad43c0bf181d86dfedb03d
Source dataset
uspto-grants-2003_05
Patent number
US06569849B1

Reaction notes

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