Ammonium Chloride → (7-Chloro-1,3-dioxaindan-5-yl)methanol

HRID 1847674Notes

Reaction equation

HRID 1847674 reaction equation
[Cl:1][C:2]1[C:7]2[O:8][CH2:9][O:10][C:6]=2[CH:5]=[C:4]([CH:11]=[O:12])[CH:3]=1.[BH4-].[Na+].[NH4+].[Cl-]>C1COCC1>[Cl:1][C:2]1[C:7]2[O:8][CH2:9][O:10][C:6]=2[CH:5]=[C:4]([CH2:11][OH:12])[CH:3]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 6764927-Chloro-1,3-dioxaindane-5-carbaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 4962440(7-Chloro-1,3-dioxaindan-5-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7-chlorobenzo[d][1,3]dioxole-5-carbaldehyde (6.0 g, 33 mmol) in THF (50 mL) was added NaBH4 (2.5 g, 64 mmol)) in portions at 0° C. The mixture was stirred at this temperature for 30 min and then poured into aqueous NH4Cl solution. The organic layer was separated, and the aqueous phase was extracted with EtOAc (50 mL×3). The combined extracts were dried over Na2SO4 and evaporated under reduced pressure to afford (7-chlorobenzo[d][1,3]dioxol-5-yl)methanol, which was directly used in the next step.

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous phase was extracted with EtOAc (50 mL×3)
  3. dry with materialThe combined extracts were dried over Na2SO4
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-2f266066d266412b888eac0040d7ad3b
Source dataset
uspto-grants-2015_02
Patent number
US08952049B2

Reaction notes

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