Ammonium Chloride → HCID 21260480, compound

HRID 634775Notes

Reaction equation

HRID 634775 reaction equation
[Mg].[CH2:2]([O:9][C:10]1[CH:15]=[CH:14][C:13](Br)=[CH:12][CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:17]1[O:27][C:20]2([CH2:25][CH2:24][C:23](=[O:26])[CH2:22][CH2:21]2)[O:19][CH2:18]1.[NH4+].[Cl-]>C1COCC1>[CH2:2]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:23]2([OH:26])[CH2:24][CH2:25][C:20]3([O:27][CH2:17][CH2:18][O:19]3)[CH2:21][CH2:22]2)=[CH:12][CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 1388351-Bromo-4-phenylmethoxybenzeneHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 5462224Magnesium

Product 1

HCID 21260480HCID 21260480, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of the Grignard reagent prepared from Magnesium turnings (2.33 g, 96 mmol) and 4-benzyloxybromobenzene (25 g, 95 mmol) in THF (150 ml), 1,4-Cyclohexanedione monoethylene ketal (10 g, 64 mmol) in THF (150 ml) was added. After completeion of the reaction, the solution was added to 200 ml of aq. NH4Cl and extracted with CH2Cl2. Drying and evaporation of the organic layer gave a residue which was crystallised from AcOEt-hexane to give 8-(4-benzyloxy-phenyl)-1,4-dioxa-spiro[4.5]decan-8-ol (17.5 g, 54%, MS: m/e=340 (M+)).

Workup

  1. additionwas added
  2. customAfter completeion of the reaction
  3. extractionextracted with CH2Cl2
  4. customDrying
  5. customevaporation of the organic layer
  6. customgave a residue which
  7. customwas crystallised from AcOEt-hexane

Sources & evidence

ORD record
ord-58f98b68227a415fa47aa9b299ae6e2a
Source dataset
uspto-grants-2001_02
Patent number
US06184236B2

Reaction notes

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